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

HRID 1470309
Notes
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Reaction equation

HRID 1470309 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 674594834-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-52ea22113bd343f3861e84be36039659
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006433B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes