Triethylamine → 9-(4-Chlorothiazol-2-yl)-1,3-dimethyl-5-phenyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

HRID 2201221노트

반응식

HRID 2201221 반응식
[Cl:1][C:2]1[N:3]=[C:4]([CH:7](O)[CH2:8][CH2:9][N:10]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]3[C:12]([N:13]([CH3:28])[C:14](=[O:27])[N:15]([CH3:26])[C:16]3=[O:25])=[CH:11]2)[S:5][CH:6]=1.C(N(CC)CC)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[C:11]3[N:10]([C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[C:17]4[C:16](=[O:25])[N:15]([CH3:26])[C:14](=[O:27])[N:13]([CH3:28])[C:12]4=3)[CH2:9][CH2:8]2)[S:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 67749Trifluoromethanesulfonic anhydrideHCID 867234586-(3-(4-Chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

생성물 1

HCID 771068369-(4-Chlorothiazol-2-yl)-1,3-dimethyl-5-phenyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Trifluromethanesulfonic anhydride (0.576 mL, 3.41 mmol) in DCM (3 mL) was added slowly to a solution of 6-(3-(4-chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (490 mg, 1.137 mmol) and triethylamine (0.792 mL, 5.69 mmol) in DCM (40 mL) at 0° C. Further portions of triethylamine (0.792 mL, 5.69 mmol) and trifluoromethanesulfonic anhydride (0.576 mL, 3.41 mmol) were added to allow the reaction to run to completion. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by mass-directed HPLC under the following conditions afforded the title compound.

후처리

  1. customthe reaction
  2. customThe reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted with DCM
  4. customevaporated under vacuum
  5. customPurification by mass-directed HPLC under the following conditions

출처 및 근거

ORD 기록
ord-c6018f784b86418c93e327f0cc19d092
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359381B2

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