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

HRID 32347

반응식

HRID 32347 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-18bd44274c2b4c4e801eafef9a09ff7c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427626B2

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