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Benzyl Alcohol → Benzyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamate

HRID 1868463
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HRID 1868463 반응식
[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([CH:23]=[C:24](C(O)=O)[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1.[C:47]1([CH2:53][OH:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.CC[N:57]([CH2:60]C)CC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([CH:23]=[C:24]([NH:57][C:60]([O:54][CH2:53][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:37])[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

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HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 670215506-((Tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

생성물 1

HCID 67021499Benzyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamate수율 52.8%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a stirred solution of 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (Example 58, Step 2, 30 mg, 0.07 mmol) in PhCH3 (3 mL) was added DPPA (19 μL, 0.09 mmol), PhCH2OH (17 μL, 0.17 mmol) and Et3N (12 μL, 0.09 mmol). The reaction was heated to 100° C. for 16 h and was concentrated under reduced pressure. The resulting residue was diluted with EtOAc and extracted with satd aq NH4Cl, NaHCO3 and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded benzyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamate (20 mg, 32%).

후처리

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc
  3. extractionextracted with satd aq NH4Cl, NaHCO3 and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-e56a7c52264b4978a986ea9184e0cba8
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07635699B2

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