4-Hydroxypyrimidine → N-(5-(2-Phenylethyl)pyrimidin-4-yl)-L-phenylalanine Isopropyl Ester

HRID 18049

Reaction equation

HRID 18049 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](=O)[NH:3][CH:2]=1.[Cl:8][C:9]1[C:14](I)=[CH:13]N=CN=1.Cl.[CH:17]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:23])([CH3:19])[CH3:18]>>[ClH:8].[CH:17]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH2:23])([CH3:19])[CH3:18].[CH:17]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:23][C:4]1[C:5]([CH2:13][CH2:14][C:9]2[CH:26]=[CH:25][CH:24]=[CH:22][CH:21]=2)=[CH:6][N:1]=[CH:2][N:3]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 206954-HydroxypyrimidineHCID 112302044-Chloro-5-iodopyrimidine2×HCID 15599949propan-2-yl (2S)-2-amino-3-phenylpropanoate hydrochloride

Product 2

HCID 10318179N-(5-(2-Phenylethyl)pyrimidin-4-yl)-L-phenylalanine Isopropyl EsterHCID 15599949propan-2-yl (2S)-2-amino-3-phenylpropanoate hydrochloride

Procedure

L-Phenylalanine isopropyl ester hydrochloride was prepared by Method LLL. 4(3H)-Pyrimidinone (Aldrich) was sequentially converted via Methods N and O to 4-chloro-5-iodopyrimidine. L-Phenylalanine isopropyl ester hydrochloride and 4-chloro-5-iodopyrimidine were coupled via Method P and the coupled product sequentially converted via Methods OOO and X to give the title compound.

Sources & evidence

ORD record
ord-889fc714dc684d58a4be9bd442b37b95
Source dataset
uspto-grants-2010_06
Patent number
US07741328B2

Linked notes

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