4-(5-ethynyl-2-pyridinyl)morpholine -Drug Synthesis Database

【结构式】

【分子编号】60888

【品名】4-(5-ethynyl-2-pyridinyl)morpholine

【CA登记号】

【分子式】C₁₁H₁₂N₂O

【分子量】188.22916

【元素组成】C 70.19% H 6.43% N 14.88% O 8.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

Reaction of 2,5-dibromopyridine (I) with morpholine (II) yields 5-bromo-2-(4-morpholinyl)pyridine (III). Palladium-catalyzed coupling of (III) with trimethylsilyl acetylene (IV) leads to the ethynylpyridine (V)

参考文献中间体

合成目标

【1】 Gomtsyan, A.; et al.; Design, synthesis, and structure-activity relationship of 6-alkynylpyrimidines as potent adenosine kinase inhibitors. J Med Chem 2002, 45, 17, 3639.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	19330	2,5-dibromopyridine	624-28-2	C₅H₃Br₂N	详情	详情
(II)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(III)	60887	4-(5-bromo-2-pyridinyl)morpholine		C₉H₁₁BrN₂O	详情	详情
(IV)	51602	1-Propyne		C₃H₄	详情	详情
(V)	60888	4-(5-ethynyl-2-pyridinyl)morpholine		C₁₁H₁₂N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Iodination of 5-amino-4,6-dichloropyrimidine (VI) by means of NaI in concentrated HI affords the diiodopyridine (VII). Sequential alkylation of aminopyrimidine (VII) with 2-chlorobenzyl bromide (VIII) to produce (IX), and further N-methylation with iodomethane and NaH, lead to the tertiary amine (X). Ammonolysis of the diiodopyrimidine (X) with ethanolic ammonia in a sealed tube at 80 C yields amine (XI). Finally, Sonogashira coupling between acetylene (V) and iodopyrimidine (XI) in the presence of Pd(PPh3)2Cl2 and CuI furnishes the target diaryl acetylene

参考文献中间体

合成目标

【1】 Gomtsyan, A.; et al.; Design, synthesis, and structure-activity relationship of 6-alkynylpyrimidines as potent adenosine kinase inhibitors. J Med Chem 2002, 45, 17, 3639.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	60888	4-(5-ethynyl-2-pyridinyl)morpholine		C₁₁H₁₂N₂O	详情	详情
(VI)	22845	5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine	5413-85-4	C₄H₃Cl₂N₃	详情	详情
(VII)	60889	4,6-diiodo-5-pyrimidinamine; 4,6-diiodo-5-pyrimidinylamine		C₄H₃I₂N₃	详情	详情
(VIII)	53082	1-(Bromomethyl)-2-chlorobenzene; 2-Chloro-alpha-bromotoluene; 2-Chlorobenzyl bromide; Alpha-Bromo-2-chlorotoluene; o-Chlorobenzyl bromide	611-17-6	C₇H₆BrCl	详情	详情
(IX)	60890	N-(2-chlorobenzyl)-4,6-diiodo-5-pyrimidinamine; N-(2-chlorobenzyl)-N-(4,6-diiodo-5-pyrimidinyl)amine		C₁₁H₈ClI₂N₃	详情	详情
(X)	60891	N-(2-chlorobenzyl)-4,6-diiodo-N-methyl-5-pyrimidinamine; N-(2-chlorobenzyl)-N-(4,6-diiodo-5-pyrimidinyl)-N-methylamine		C₁₂H₁₀ClI₂N₃	详情	详情
(XI)	60892	N-(4-amino-6-iodo-5-pyrimidinyl)-N-(2-chlorobenzyl)-N-methylamine; N~5~-(2-chlorobenzyl)-6-iodo-N~5~-methyl-4,5-pyrimidinediamine		C₁₂H₁₂ClIN₄	详情	详情

Extended Information