1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

HRID 889064Notes

Reaction equation

HRID 889064 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([CH2:17][N:18]2[CH:22]=[C:21]([C:23](O)=[O:24])[CH:20]=[N:19]2)[CH2:3]1.[NH2:26][C:27]1[C:28](=[O:38])[N:29]([CH2:35][CH2:36][CH3:37])[C:30](=[O:34])[NH:31][C:32]=1[NH2:33].CCN=C=NCCCN(C)C>CO>[NH2:33][C:32]1[NH:31][C:30](=[O:34])[N:29]([CH2:35][CH2:36][CH3:37])[C:28](=[O:38])[C:27]=1[NH:26][C:23]([C:21]1[CH:20]=[N:19][N:18]([CH2:17][CH:4]2[CH2:3][C:2](=[O:1])[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=3)[CH2:5]2)[CH:22]=1)=[O:24]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 579887561-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid

Product 1

HCID 579887631-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amideYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (1 g, 2.83 mmol) and 5,6-Diamino-3-propyl-1H-pyrimidine-2,4-dione (521 mg, 2.83 mmol) in MeOH (40 mL) was added EDCI (813 mg, 4.24 mmol) under argon atmosphere. After stirring at overnight at room temperature the reaction mixture was quenched with water (10 mL) and white solid was precipitated out. The solid was filtered and washed with water to give the crude product which on purification by column chromatography (eluting with 5% MeOH:DCM) furnished the title compound as a white solid (1.3 g, 88%).

Workup

  1. customwas quenched with water (10 mL) and white solid
  2. customwas precipitated out
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customto give the crude product which
  6. customon purification
  7. washby column chromatography (eluting with 5% MeOH:DCM)

Sources & evidence

ORD record
ord-00b5f378aed94b1a9292dca1f90ccc90
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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