Cesium carbonate → 4-(4-Benzylpiperazin-1-yl)-6-chloropyrimidin-2-amine

HRID 1893173Notes

Reaction equation

HRID 1893173 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[C:17]([Cl:22])[N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[CH:18]=[C:17]([Cl:22])[N:16]=[C:15]([NH2:14])[N:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 759941-Benzylpiperazine

Product 1

HCID 315376104-(4-Benzylpiperazin-1-yl)-6-chloropyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Benzyl-piperazine (5.86 g, 33.3 mmol), 2-amino-4,6-dichloro-pyrimidine (5.46 g, 33.3 mmol) and Cs2CO3 (10.8 g, 36.6 mmol) were combined in anhydrous N,N-dimethylformamide (DMF) (50 mL) and stirred at 90° C. in dry atmosphere for 5 h. The DMF was removed in vacuo, the residue was dissolved in acetone, and 4-(4-Benzyl-piperazin-1-yl)-6-chloro-pyrimidin-2-ylamine (8.5 g, 86%) was is crystallized form acetone.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was dissolved in acetone
  3. custom4-(4-Benzyl-piperazin-1-yl)-6-chloro-pyrimidin-2-ylamine (8.5 g, 86%) was is crystallized form acetone

Sources & evidence

ORD record
ord-7e175defcf03431eb8e35dfff111557d
Source dataset
uspto-grants-2013_08
Patent number
US08513233B2

Reaction notes

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