4,6-Dimethoxypyrimidine-5-carbaldehyde → 2,6-Diamino-4-(4,6-dimethoxypyrimid-5-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 328220

Reaction equation

HRID 328220 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=O)=[C:7]([O:11][CH3:12])[N:6]=[CH:5][N:4]=1.[CH2:13]([O:15][C:16](=[O:21])[CH2:17][C:18](=[NH:20])[NH2:19])[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[CH:9]([C:8]2[C:7]([O:11][CH3:12])=[N:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1])[C:17]([C:16]([O:15][CH2:13][CH3:14])=[O:21])=[C:18]([NH2:19])[NH:20][C:18]=1[NH2:19])=[O:21])[CH3:14]

Participants

4

Reactant 2

HCID 44366454,6-Dimethoxypyrimidine-5-carbaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 706316852,6-Diamino-4-(4,6-dimethoxypyrimid-5-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon heating a solution of 8.4 g 4,6-dimethoxypyrimidine-5-aldehyde and 13.0 g amidinoacetic acid ethyl ester in 150 ml ethanol for two hours, 2,6-diamino-4-(4,6-dimethoxypyrimid-5-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of m.p. 219° C (ethanol) is obtained.

Sources & evidence

ORD record
ord-08b4ebf3ee474842b90c1ffd1be5e988
Source dataset
uspto-grants-1977_04
Patent number
US04016277

Linked notes

Loading…