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Water → 3-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,8,10-tetrahydro-4H-pyrimido[2,1-c][1,4]oxazepine-2-carboxylic acid

HRID 1788117
Notes
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Reaction equation

HRID 1788117 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]([C:9]1[NH:10][C:11](=[O:21])[C:12]([OH:20])=[C:13]([C:15]([O:17]CC)=[O:16])[N:14]=1)([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C)C=O>[CH2:28]([O:20][C:12]1[C:11](=[O:21])[N:10]2[C:9]([C:6]([CH3:7])([CH3:8])[O:5][CH2:4][CH2:3][CH2:2]2)=[N:14][C:13]=1[C:15]([OH:17])=[O:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135848641Ethyl 2-(2-(3-chloropropoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 210698553-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,8,10-tetrahydro-4H-pyrimido[2,1-c][1,4]oxazepine-2-carboxylic acidYield 135.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of intermediate 33, ethyl 2-(2-(3-chloropropoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (0.205 g, 0.64 mmol) and anhydrous potassium carbonate (0.361 g, 2.6 mmol) in anhydrous dimethylformamide (4 mL) was stirred at 60° C. for 5 hours. The reaction mixture was treated with benzyl bromide (0.122 g, 0.71 mmol) and stirred for 16 hours. Following this, 2 mL of H2O was added and the mixture stirred for an additional 24 hours. Solvent was removed by rotary evaporator and the resulting residue suspended in 0.5 N hydrochloric acid (16 mL). The crude product was extracted with ethyl acetate (2×15 mL), then dried (sodium sulfate), filtered, and concentrated to dryness by rotary evaporator to give 0.299 g (Yield >100%) of the title compound as a solid. LC/MS [M+H]+=345.21.

Workup

  1. stirringstirred for 16 hours
  2. additionwas added
  3. stirringthe mixture stirred for an additional 24 hours
  4. customSolvent was removed by rotary evaporator
  5. extractionThe crude product was extracted with ethyl acetate (2×15 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness by rotary evaporator

Sources & evidence

ORD record
ord-ab0304298cbf48caa8874bbebe443ba8
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07511037B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes