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

HRID 2175903ノート

反応式

HRID 2175903 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f851af3a751140f1915c567b8ce03c50
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

反応ノート

読み込み中…