Cyclopropanecarboxaldehyde → 4-(6-bromo-2-cyclopropyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

HRID 1398508ノート

反応式

HRID 1398508 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.[CH:17]1([CH:20]=O)[CH2:19][CH2:18]1.OOS([O-])=O.[K+]>CN(C=O)C.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([CH:17]3[CH2:19][CH2:18]3)[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:3]=2[CH:4]=1

参加物

6

反応物 3

HCID 123114CyclopropanecarboxaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 681818104-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

生成物 1

HCID 681817554-(6-bromo-2-cyclopropyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (400 mg, 1.43 mmol) in DMF (4 mL) were added cyclopropanecarbaldehyde (130 mg, 1.86 mmol) and oxone (527 mg, 0.86 mmol). The reaction was stirred at RT for 3 days. The mixture was diluted with EtOAc (20 mL) and washed with water. The aqueous layer was extracted with more EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (Isolute column, 100% DCM to 2% MeOH/DCM) afforded the title compound as an orange solid: 1H NMR (500 MHz, MeOD) δ 1.16-1.24 (2H, m), 1.24-1.29 (2H, m), 2.32-2.48 (1H, m), 6.98 (1H, d, J=5.36 Hz), 7.41-7.45 (1H, m), 7.47-7.52 (1H, m), 7.90 (1H, d, J=1.89 Hz), 8.51 (1H, d, J=5.20 Hz); LC-MS (Method B): m/z=+330.0, 331.8 (M+H)+.

後処理

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with more EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (Isolute column, 100% DCM to 2% MeOH/DCM)

出典と根拠

ORDレコード
ord-88fa5fdb471a43f99cb0a4e019655ef5
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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