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 1713184Notes

Reaction equation

HRID 1713184 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-9deb6e2eff804ea8ae731fe11faccfa9
Source dataset
uspto-grants-2010_09
Patent number
US07795268B2

Reaction notes

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