Potassium Carbonate → HCID 86634078, compound

HRID 1041736Notes

Reaction equation

HRID 1041736 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([Cl:9])=[N:6][C:7]=1Cl.[CH3:10][NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:9][C:5]1[N:6]=[C:7]([N:19]([CH3:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([NH:11][CH3:10])=[O:21])[C:2]([F:1])=[CH:3][N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 1093177832212-33-2

Product 1

HCID 86634078HCID 86634078, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2,6-dichloropyrimidine (1.0 g, 6 mmol, 2.0 eq.), N-methyl-2-methylamino-benzamide (0.5 g, 3 mmol), and potassium carbonate (0.85 g, 6 mmol, 2.0 eq.) was stirred in DMF (100 mL) for 24 h. The solvent was removed under high vacuum and the residue was purified on silica gel with DCM/MeOH (9.5/0.5) to give 2-[(2-chloro-5-fluoro-pyrimidin-4-yl)-methyl-amino]-N-methyl-benzamide (230 mg, 26%): 1H NMR (300 MHz, CD3OD) δ 7.93 (dd, 1H), 7.73 (dd, 1H), 7.6 (m, 3H), 3.09 (s, 3H), 2.97 (s, 3H).

Workup

  1. customThe solvent was removed under high vacuum
  2. customthe residue was purified on silica gel with DCM/MeOH (9.5/0.5)

Sources & evidence

ORD record
ord-5ea6b6bfa84745b79831d0b0af51e639
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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