Dimethylformamide → methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

HRID 1853051노트

반응식

HRID 1853051 반응식
Cl.[NH:2]1[CH:6]=[C:5]([C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[N:8]=2)[CH:4]=[N:3]1.[CH:20]1([CH:23]=[CH:24][C:25]#[N:26])[CH2:22][CH2:21]1.CN(C=O)C.C1CCN2C(=NCCC2)CC1>CCOC(C)=O>[C:25]([CH2:24][CH:23]([N:2]1[CH:6]=[C:5]([C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[N:8]=2)[CH:4]=[N:3]1)[CH:20]1[CH2:22][CH2:21]1)#[N:26]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 670567823-CyclopropylacrylonitrileHCID 86685326methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochloride

생성물 1

HCID 67456699methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate수율 35.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

In a 100 mL flask, methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochloride (0.300 g, 1.07 mmol) and 3-cyclopropylacrylonitrile (Preparation B; 0.300 g, 3.22 mmol) were suspended in DMF (5.36 mL, 1.07 mmol) and DBU (0.722 mL, 4.83 mmol) added in one portion. The reaction mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted in EtOAc and washed with water and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated down to a yellow oil. Purification of the crude material by silica chromatography using a gradient of 50-100% EtOAc afforded methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (0.127 g, 0.378 mmol, 35.2% yield) as a yellow oil. MS (apci) m/z=337.2 (M+H).

후처리

  1. washwashed with water and brine
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down to a yellow oil
  5. customPurification of the crude material by silica chromatography

출처 및 근거

ORD 기록
ord-e59a4f1628a04ba2a0d5554684cf527b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

반응 노트

불러오는 중…