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

HRID 1246233Notes

Reaction equation

HRID 1246233 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH2:12][CH2:13][CH3:14])[C:5](=O)[N:6](CC)[C:7]=1[NH2:8].[F:16][C:17]([F:34])([F:33])[C:18]1[CH:19]=[C:20]([CH2:24][N:25]2[CH:29]=[C:28]([C:30]([OH:32])=O)[CH:27]=[N:26]2)[CH:21]=[CH:22][CH:23]=1.Cl.CN(C)CCCN=C=N[CH2:44][CH3:45].C[OH:48]>>[NH2:8][C:7]1[NH:6][CH2:5][N:4]([CH:12]([CH2:13][CH3:14])[C:44](=[O:48])[CH3:45])[C:3](=[O:15])[C:2]=1[NH:1][C:30]([C:28]1[CH:27]=[N:26][N:25]([CH2:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:34])[F:33])[CH:19]=2)[CH:29]=1)=[O:32]

Participants

5

Reactant 4

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114927411-(3-(Trifluoromethyl)benzyl)-1H-pyrazole-4-carboxylic acidHCID 219163965,6-diamino-1-ethyl-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 131726002n-(6-Amino-1-ethyl-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-1-ethyl-3-propyl-1,3-dihydropyrimidine-2,4-dione (100 mg, 0.47 mmol) and 1-{[3-(trifluoromethyl)phenyl]methyl}pyrazole-4-carboxylic acid (0.151 g, 0.56 mmol) in methanol (10 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.135 g, 0.7 mmol), and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure, and the residue purified using Bistag, eluting with 10% methanol/methylene chloride, to provide N-(6-amino-1-ethyl-2,4-dioxo-3-propyl(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl}-pyrazol-4-yl)carboxamide.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified
  3. washeluting with 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-6930213b8aa648a1853a41be245afa31
Source dataset
uspto-grants-2006_10
Patent number
US07125993B2

Reaction notes

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