Ethyl orthoformate → Methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

HRID 2175903노트

반응식

HRID 2175903 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=2[N:7]=1.FC(F)(F)C(O[Si](C)(C)C)=O.[CH:26](OCC)(OCC)OCC.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38]>C(OCC)(=O)C>[N:1]1([C:2]2[N:3]=[CH:4][C:5]3[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=3[N:7]=2)[CH:26]=[N:36][N:37]=[N:38]1

참가 물질

6

반응물 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 86727099Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

생성물 1

HCID 86727101Methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate (65.2 mg, 0.364 mmol) in ethyl acetate (5 mL) was added trimethylsilyl trifluoroacetate (0.107 mL, 0.619 mmol) at room temperature. The mixture was stirred at room temperature then triethyl orthoformate (0.103 mL, 0.619 mmol) was added. The mixture was stirred for another 5 minutes then azidotrimethylsilane (0.081 mL, 0.619 mmol) was added. The reaction was stirred at room temperature overnight then concentrated in vacuo and the residue was triturated twice with dichloromethane. The resulting solid was collected by centrifugation and dried in vacuo to afford the title compound: LC/MS: [(M+1)]+=233.

후처리

  1. stirringThe mixture was stirred for another 5 minutes
  2. stirringThe reaction was stirred at room temperature overnight
  3. concentrationthen concentrated in vacuo
  4. customthe residue was triturated twice with dichloromethane
  5. customThe resulting solid was collected by centrifugation
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-f851af3a751140f1915c567b8ce03c50
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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