Cesium carbonate → HCID 68182024, compound

HRID 1398691Notes

Reaction equation

HRID 1398691 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10](Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-:28].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:28])[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 68182024HCID 68182024, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol), pyrrolidine (1 mL) and cesium carbonate (2 g, 6.14 mmol) in N,N-dimethylformamide (5 mL) was stirred for 24 h at room temperature. The reaction mixture was purified on a C18 column (acetonitrile/water, 5:95-80:20) to give 240 mg (51%) of 4-[6-bromo-2-[(pyrrolidin-1-yl)carbonyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a white solid: 1H NMR (300 MHz, DMSO) delta 8.42 (d, J=5.1 Hz, 1H), 8.11 (d, J=1.8 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.57-7.53 (m, 1H), 7.07 (s, 2H), 6.71 (d, J=5.4 Hz, 1H), 3.60 (d, J=6.3 Hz, 2H), 3.50 (t, J=6.6 Hz, 2H), 1.92 (s, 4H); LC-MS: m/z=+387 (M+H)+.

Workup

  1. customThe reaction mixture was purified on a C18 column (acetonitrile/water, 5:95-80:20)

Sources & evidence

ORD record
ord-448afb8cca9d41a0a17463b5e22979b0
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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