Water → HCID 59579911, compound

HRID 2279609Notes

Reaction equation

HRID 2279609 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([C:11]([F:14])([F:13])[F:12])=[N:4]1)C.ClC1[N:21]=[C:20]([NH2:22])[C:19]([F:23])=[CH:18][N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].O.CN1C(=O)C[CH2:34][CH2:33]1>>[NH2:22][C:20]1[C:19]([F:23])=[CH:18][N:17]=[C:1]([N:3]2[CH:7]=[C:6]([C:8]([O:10][CH2:33][CH3:34])=[O:9])[C:5]([C:11]([F:14])([F:13])[F:12])=[N:4]2)[N:21]=1

Participants

6

Reactant 5

HCID 962WaterHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 2543722-Chloro-5-fluoropyrimidin-4-amineHCID 18996921155377-11-0

Product 1

HCID 59579911HCID 59579911, compound

Procedure

A solution of ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (150 mg, 0.72 mmol), 2-chloro-5-fluoro-pyrimidin-4-ylamine (102 mg, 0.79 mmol) and Cs2CO3 (325 mg, 1 mmol) in NMP (1.0 mL) is heated in a microwave reactor at 150° C. for 1 h. The mixture is poured into H2O. The crude product is filtered out, dissolved in 10% MeOH in DCM, and dried over anhydrous Na2SO4. The title compound is purified by PTLC (eluted with 5% MeOH in DCM).

Workup

  1. filtrationThe crude product is filtered out
  2. dissolutiondissolved in 10% MeOH in DCM
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe title compound is purified by PTLC (eluted with 5% MeOH in DCM)

Sources & evidence

ORD record
ord-00321c88b3e242268feb0fbfeac0b172
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

Loading…