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Water → [2-(4-Methoxy-5-nitro-pyrimidin-2-yloxy)-ethyl]-propyl-carbamic acid tert-butyl ester

HRID 390293
Notes
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Reaction equation

HRID 390293 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:18]1[N:23]=[C:22]([O:24][CH3:25])[C:21]([N+:26]([O-:28])=[O:27])=[CH:20][N:19]=1.O>C1COCC1>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12][O:13][C:18]1[N:23]=[C:22]([O:24][CH3:25])[C:21]([N+:26]([O-:28])=[O:27])=[CH:20][N:19]=1)[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 38016162-Chloro-4-methoxy-5-nitropyrimidineHCID 14925143(2-Hydroxy-ethyl)-propyl-carbamic acid tert-butyl ester

Product 1

HCID 66882150[2-(4-Methoxy-5-nitro-pyrimidin-2-yloxy)-ethyl]-propyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a solution of (2-hydroxy-ethyl)-propyl-carbamic acid tert-butyl ester (1.07 g, 5.28 mmol) in THF (40 ml) at 0° C. was added NaH (0.25 g, 5.80 mmol). After stirring the suspension at 0° C. for 30 minutes a solution of 2-chloro-4-methoxy-5-nitropyrimidine (1 g, 5.28 mmol) in THF (10 ml) was added and the mixture was stirred at room temperature for 16 h. The mixture was added to water, which was extracted three times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to obtain the title compound.

Workup

  1. additionwas added
  2. extractionwas extracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-655a99571ab9415eb30d5c8a6b6fe233
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes