4-Amino-2-chloropyrimidine-5-carbonitrile → 4-Amino-5-cyano-2-{4-[N-(3-hydroxy-2,2-dimethylpropyl)sulphamoyl]anilino}pyrimidine

HRID 1071352Notes

Reaction equation

HRID 1071352 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[OH:11][CH2:12][C:13]([CH3:27])([CH3:26])[CH2:14][NH:15][S:16]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CN1C(=O)CCC1.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:23][C:22]2[CH:24]=[CH:25][C:19]([S:16](=[O:18])(=[O:17])[NH:15][CH2:14][C:13]([CH3:26])([CH3:27])[CH2:12][OH:11])=[CH:20][CH:21]=2)[N:3]=1

Participants

5

Reactant 2

HCID 28011664-Amino-2-chloropyrimidine-5-carbonitrileHCID 219562104-amino-N-(3-hydroxy-2,2-dimethyl-propyl)benzenesulfonamide

Product 1

HCID 223932704-Amino-5-cyano-2-{4-[N-(3-hydroxy-2,2-dimethylpropyl)sulphamoyl]anilino}pyrimidineYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-amino-2-chloro-5-cyanopyrimidine (150 mg, 0.97 mmol), 4-[N-(3-hydroxy-2,2-dimethylpropyl)sulphamoyl]aniline (Method 4; 274 mg, 1.07 mmol) in NMP (5 ml) was heated at 120° C. for 24 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried and the solvent removed by evaporation, the residue was triturated with ether and the product collected by filtration to give the title compound (187 mg, 52%). NMR: 0.72 (s, 6H), 2.52 (d, 2H), 3.08 (d, 2H), 4.40 (t, 1H), 7.19 (t, 1H), 7.60 (s, 1H), 7.64 (d, 2H), 7.96 (d, 2H), 8.40 (s, 1H); m/z 375 (M−H)−.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customthe solvent removed by evaporation
  5. customthe residue was triturated with ether
  6. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-1243e98c23f74a7c94d5e89ba19476d3
Source dataset
uspto-grants-2005_06
Patent number
US06906065B2

Reaction notes

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