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Trifluoroacetic acid → 9-(4-chlorothiazol-2-yl)-5-(3-fluorophenyl)-7-(hydroxymethyl)-1,3-dimethyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

HRID 2201262
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HRID 2201262 반응식
FC(F)(F)C(O)=O.[Si]([O:15][CH2:16][CH:17]1[CH2:24][CH:23]([C:25]2[S:26][CH:27]=[C:28]([Cl:30])[N:29]=2)[C:22]2[N:18]1[C:19]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=1)=[C:20]1[C:34](=[O:35])[N:33]([CH3:36])[C:32](=[O:37])[N:31]([CH3:38])[C:21]1=2)(C(C)(C)C)(C)C>CO.O>[Cl:30][C:28]1[N:29]=[C:25]([CH:23]2[C:22]3[N:18]([C:19]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=4)=[C:20]4[C:34](=[O:35])[N:33]([CH3:36])[C:32](=[O:37])[N:31]([CH3:38])[C:21]4=3)[CH:17]([CH2:16][OH:15])[CH2:24]2)[S:26][CH:27]=1
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참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 867235027-(((tert-Butyldimethylsilyl)oxy)methyl)-9-(4-chlorothiazol-2-yl)-5-(3-fluorophenyl)-1,3-dimethyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

생성물 1

HCID 771076329-(4-chlorothiazol-2-yl)-5-(3-fluorophenyl)-7-(hydroxymethyl)-1,3-dimethyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매
2회

실험 절차

Trifluoroacetic acid (2 mL, 26.0 mmol) was added to a solution of 7-(((tert-butyldimethylsilyl)oxy)methyl)-9-(4-chlorothiazol-2-yl)-5-(3-fluorophenyl)-1,3-dimethyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione (570 mg, 0.991 mmol) in methanol (20 mL) and water (3 mL). The mixture stirred at room temperature 20 mins. Further portions of water (1 mL) and trifluoroacetic acid (1 mL) were added and the mixture stirred for a further 3 hours. The reaction was quenched with saturated NaHCO3(aq) and extracted with chloroform (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane afforded the title compounds as a mixture of diastereomers.

후처리

  1. stirringthe mixture stirred for a further 3 hours
  2. customThe reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted with chloroform (3×)
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 0-100% EtOAc/hexane

출처 및 근거

ORD 기록
ord-2be1fd51d0eb446d9e04afea55e85d65
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359381B2

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