Hydrochloric Acid → 1-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1091686노트

반응식

HRID 1091686 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.Cl[CH2:13][C:14]1[NH:15][C:16](=[O:24])[C:17]2[CH:22]=[C:21]([CH3:23])[S:20][C:18]=2[N:19]=1.CC(C)([O-])C.[K+].Cl>C1COCC1.CCOC(C)=O.O.CN(C=O)C>[CH3:23][C:21]1[S:20][C:18]2[N:19]=[C:14]([CH2:13][N:5]3[CH:6]=[C:7]([CH:8]=[O:9])[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4]3)[NH:15][C:16](=[O:24])[C:17]=2[CH:22]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 64916832-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23665647Potassium tert-butoxideHCID 178519884HCID 178519884, 화합물

생성물 1

HCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde수율 58.4%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매3회

실험 절차

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde (3.82 g, 23.3 mmol) and 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (5.00 g, 23.3 mmol) were suspended in THF:DMF (180 mL:20 mL) and potassium tert-butoxide (5.23 g, 46.6 mmol) added. The resulting mixture was stirred at RT for 18 h. The mixture was then diluted with EtOAc (500 mL) and shaken with water (200 mL). The separated aqueous phase was acidified to pH 5 with dilute HCl solution and reshaken with the organic layer. The separated organics were then washed with brine (2×200 mL) and dried over MgSO4 before concentration in vacuo. Purification by flash column chromatography-silica gel and elution with 50% isohexane:EtOAc, then EtOAc, gave the desired product as a pale yellow solid (4.65 g, 13.6 mmol, 58%).

후처리

  1. washThe separated organics were then washed with brine (2×200 mL)
  2. dry with materialdried over MgSO4 before concentration in vacuo
  3. customPurification
  4. washby flash column chromatography-silica gel and elution with 50% isohexane

출처 및 근거

ORD 기록
ord-383d8b75bd524d6aa21db07431ec43db
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129397B2

반응 노트

불러오는 중…