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

HRID 2175928ノート

反応式

HRID 2175928 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3803130d5664412cb87665a2a57c85cb
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

反応ノート

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