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 1912500Notes

Reaction equation

HRID 1912500 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-f64fbe7f7390498c9e1a12f25bc470e4
Source dataset
uspto-grants-2013_12
Patent number
US08609671B2

Reaction notes

Loading…