2-Amino-4,6-dimethoxypyrimidine → (2S,4EZ)-4-[(benzyloxy)imino]-N-(4,6-dimethoxy-2-pyrimidinyl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349052Notes

Reaction equation

HRID 1349052 reaction equation
[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17]C(C)(C)C)=O)[C@H:12]([C:22]([OH:24])=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]=[C:26]1[C:31](C(Cl)=O)=[CH:30][CH:29]=[C:28]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[O:27]1.[CH3:40][O:41][C:42]1[CH:47]=[C:46]([O:48][CH3:49])[N:45]=[C:44]([NH2:50])[N:43]=1>>[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([C:31]2[C:26](=[O:25])[O:27][C:28]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:29][CH:30]=2)=[O:17])[C@H:12]([C:22]([NH:50][C:44]2[N:43]=[C:42]([O:41][CH3:40])[CH:47]=[C:46]([O:48][CH3:49])[N:45]=2)=[O:24])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725434(2S,4EZ)-4-[(benzyloxy)imino]-N-(4,6-dimethoxy-2-pyrimidinyl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 4,6-dimethoxy-2-pyrimidinamine the title compound was obtained in 62% purity by LC/MS. MS(ESI+): m/z=564.6.

Sources & evidence

ORD record
ord-d4744a0ddfe54ae4bf9d60ff3586a8f7
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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