1H-Pyrazol-3-amine, 5-methyl- → HCID 178419098、化合物

HRID 11831

反応式

HRID 11831 の反応式
Cl[C:2]1[C:3]2[CH:17]=[CH:16][CH:15]=[N:14][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1>C1COCC1>[CH3:24][C:22]1[CH:23]=[C:19]([NH:18][C:2]2[C:3]3[CH:17]=[CH:16][CH:15]=[N:14][C:4]=3[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:7]=2)[NH:20][N:21]=1

参加物

4

反応物 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 122038704-Chloro-2-phenylpyrido[2,3-D]pyrimidine

生成物 1

HCID 178419098HCID 178419098、化合物収率 50.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a solution of 4-chloro-2-phenyl-pyrido[2,3-d]pyrimidine (J. Pharm. Belg., 29, 1974, 145–148) (109 mg, 0.45 mmol) in THF (15 mL) was added 3-amino-5-methyl pyrazole (48 mg, 0.5 mmol) and the resulting mixture heated at 65° C. overnight. The mixture was cooled to room temperature and the resulting suspension was filtered and washed with Et2O. The solid was dissolved in a mixture EtOH:water and the pH adjusted to pH 7. The aqueous was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, DCM-MeOH gradient) to afford IV-31 as an off-white solid (69 mg, 50%): mp 234° C.; 1H NMR (DMSO) δ 2.14 (3H, s), 5.99 (1H, s), 7.20–7.40 (3H, m), 7.40–7.50 (3H, m), 8.60 (1H, d), 8.79 (1H, d), 12.82 (1H, br s); IR (solid) 2957, 2921, 2857, 1644, 1560, 1459, 1427; MS 303.2 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe resulting suspension was filtered
  3. washwashed with Et2O
  4. dissolutionThe solid was dissolved in a mixture EtOH
  5. extractionThe aqueous was extracted twice with ethyl acetate
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (SiO2, DCM-MeOH gradient)

出典と根拠

ORDレコード
ord-74bd5f909fdd45cab060be5e2f1707cd
出典データセット
uspto-grants-2006_08
特許番号
US07098330B2

関連ノート

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