Methanol → n-(6-Amino-2,4-dioxo-3-propyl(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl}pyrazol-4-yl)carboxamide

HRID 1258027Notes

Reaction equation

HRID 1258027 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[N:4]([CH2:10][CH2:11][CH3:12])[C:5](=O)[NH:6][C:7]=1[NH2:8].[F:14][C:15]([F:32])([F:31])[C:16]1[CH:17]=[C:18]([CH2:22][N:23]2[CH:27]=[C:26]([C:28](O)=[O:29])[CH:25]=[N:24]2)[CH:19]=[CH:20][CH:21]=1.Cl.CN(C)CCCN=C=NCC.C[OH:46]>>[NH2:8][C:7]1[NH:6][CH2:5][N:4]([CH2:10][C:11](=[O:46])[CH3:12])[C:3](=[O:13])[C:2]=1[NH:1][C:28]([C:26]1[CH:25]=[N:24][N:23]([CH2:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:14])([F:32])[F:31])[CH:17]=2)[CH:27]=1)=[O:29]

Participants

5

Reactant 4

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 114927411-(3-(Trifluoromethyl)benzyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 131726003n-(6-Amino-2,4-dioxo-3-propyl(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl}pyrazol-4-yl)carboxamide

Procedure

To a mixture of 5,6-diamino-3-propyl-1,3-dihydropyrimidine-2,4-dione (2.3 g, 126 mmol) and 1-{[3-(trifluoromethyl)phenyl]methyl}pyrazole-4-carboxylic acid (3.79 g, 14 mmol) in methanol (50 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.67 g, 14 mmol), and the reaction mixture was stirred for 3 days at room temperature (although less time is acceptable). The precipitate was filtered off, and was washed sequentially with water, and methanol. The product was dried under vacuum to provide N-(6-amino-2,4-dioxo-3-propyl(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl}pyrazol-4-yl)carboxamide, a compound of formula (13).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwas washed sequentially with water, and methanol
  3. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-f69fa61edad043a4b89fdb3c0a272119
Source dataset
uspto-grants-2013_06
Patent number
US08466129B2

Reaction notes

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