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

HRID 2175928노트

반응식

HRID 2175928 반응식
FC(F)(F)C(O[Si](C)(C)C)=O.[NH2:12][C:13]1[N:14]=[CH:15][C:16]2[CH:21]([C:22]([OH:24])=[O:23])[CH2:20][CH2:19][C:17]=2[N:18]=1.[CH:25](OCC)(OCC)OCC.[N:35]([Si](C)(C)C)=[N+:36]=[N-:37]>C(OCC)(=O)C>[N:12]1([C:13]2[N:14]=[CH:15][C:16]3[CH:21]([C:22]([OH:24])=[O:23])[CH2:20][CH2:19][C:17]=3[N:18]=2)[CH:25]=[N:35][N:36]=[N:37]1

참가 물질

6

반응물 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 838618122-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylic acid

생성물 1

HCID 712737752-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Trimethylsilyl trifluoroacetate (1.5 mL, 8.7 mmol) was added to a suspension of 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylic acid (845 mg, 4.72 mmol) in ethyl acetate (10 mL). A solution was obtained but a precipitate formed within 5 minutes. The reaction mixture was stirred at RT for 5 minutes and triethyl orthoformate (1.4 mL, 8.4 mmol) was added. The mixture was stirred at RT for 5 minutes and azidotrimethylsilane (1.1 mL, 8.4 mmol) was added. The resulting suspension was stirred at RT overnight. The solvent was evaporated. The residue was purified by chromatography on silica gel (80 g cartridge) using CH2Cl2 (A) and CH2Cl2:MeOH:AcOH 90:10:1 (B) with gradient elution (100% A to 100% B over 16 column volumes) to afford crude product which was further purified by preparative HPLC to afford the title compound: NMR 500 MHz (CD3OD) 10.00 (s, 1H); 8.88 (s, 1H); 4.32 (t, 1H); 3.11-3.15 (m, 2H); 2.47-2.63 (m, 2H); LC/MS (M+Na)+ at 255, (M+1)+ at 233, (M+1-N2)+ at 205.

후처리

  1. customA solution was obtained
  2. customa precipitate formed within 5 minutes
  3. stirringThe mixture was stirred at RT for 5 minutes
  4. stirringThe resulting suspension was stirred at RT overnight
  5. customThe solvent was evaporated
  6. customThe residue was purified by chromatography on silica gel (80 g cartridge)
  7. washwith gradient elution (100% A to 100% B over 16 column volumes)
  8. customto afford crude product which
  9. customwas further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-3803130d5664412cb87665a2a57c85cb
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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