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Benzyl Alcohol → Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidin-5-ylcarbamate

HRID 1470309
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HRID 1470309 반응식
[CH2:1]([O:8][C:9]1[C:14](C(O)=O)=[CH:13][N:12]=[C:11]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:25]([CH2:28]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1.[CH2:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([NH:25][C:28](=[O:37])[O:54][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:13][N:12]=[C:11]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 674594834-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid2회

생성물 1

HCID 67459577Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidin-5-ylcarbamate

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid, 3-c, (2 g, 6.76 mmol) in dry THF (40 ml) and toluene (40 ml) were added Et3N (2.04 g, 20.3 mmol), DPPA (2.04 g, 7.43 mmol) and benzyl alcohol (1.1 g, 10.1 mmol). The resulting mixture was heated at 60° C. for 12 hours. The mixture was concentrated under vacuum and the residue was purified on silica gel column with the eluent of ethyl acetate/petroleum ether=1/5 (Rf=0.6) to provide the compound, 3-d (1.96 g, 72.6%). 1H NMR (DMSO-d6, 300 MHz): δ 9.39 (br, 1H), 8.73 (s, 1H), 8.62 (s, 1H), 7.83 (s, 1H), 7.56 (m, 2H), 7.33 (m, 8H), 6.57 (m, 1H), 5.58 (s, 2H), 5.16 (s, 2H).

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified on silica gel column with the eluent of ethyl acetate/petroleum ether=1/5 (Rf=0.6)
  3. customto provide the compound, 3-d (1.96 g, 72.6%)

출처 및 근거

ORD 기록
ord-52ea22113bd343f3861e84be36039659
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006433B2

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