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

HRID 1071352
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HRID 1071352 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-1243e98c23f74a7c94d5e89ba19476d3
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06906065B2

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