Dimethylformamide → 2-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

HRID 32347

反応式

HRID 32347 の反応式
C([Li])CCC.[CH:6]([N:9]1[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:15]=2)=[CH:12][N:11]=[CH:10]1)([CH3:8])[CH3:7].CN([CH:30]=[O:31])C>C1COCC1>[NH:20]([C:16]1[N:15]=[C:14]([C:13]2[N:9]([CH:6]([CH3:8])[CH3:7])[C:10]([CH:30]=[O:31])=[N:11][CH:12]=2)[CH:19]=[CH:18][N:17]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 692226662-Anilino-4-(1-isopropylimidazole-5-yl)pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

n-Butyllithium (7.2 ml of 1.6 M solution in hexane, 11.2 mmol) was added to a solution of 4-(1-isopropylimidazol-5-yl)-2-anilinopyrimidine (Method 5; 1.25 g, 4.48 mmol) in anhydrous THF (50 ml) cooled to −70° C., and the reaction mixture was then stirred at −70° C. for 30 minutes. Anhydrous DMF (0.7 ml, 9.0 mmol) was added and the mixture was stirred for 18 hour at ambient temperature. The mixture was quenched with water (50 ml), and was extracted with EtOAc (4×75 ml). The organic extracts were combined, washed with brine (2×50 ml), dried and evaporated. The residue was purified by chromatography eluting with EtOAc/Hexane (1:1) to give the title compound (930 mg, 68%) as a pale yellow crystalline solid. NMR (CDCl3): 1.6 (d, 6H), 5.60-5.75 (m, 1H), 6.98 (d, 1H), 7.12 (t, 1H) , 7.30-7.40 (m, 3H), 7.55-7.65 (m, 3H), 8.50(d, 1H), 9.90 (s, 1H); m/z 308.

後処理

  1. stirringthe mixture was stirred for 18 hour at ambient temperature
  2. customThe mixture was quenched with water (50 ml)
  3. extractionwas extracted with EtOAc (4×75 ml)
  4. washwashed with brine (2×50 ml)
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography
  8. washeluting with EtOAc/Hexane (1:1)

出典と根拠

ORDレコード
ord-18bd44274c2b4c4e801eafef9a09ff7c
出典データセット
uspto-grants-2008_09
特許番号
US07427626B2

関連ノート

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