Benzyl Bromide → Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate

HRID 1470303Notes

Reaction equation

HRID 1470303 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([O:1][C:2]1[C:7]([C:8]([O:10][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:9])=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[N:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178524762HCID 178524762, compound

Product 1

HCID 67459462Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid, 2-c, (1 g, 4.85 mmol) in DMF (40 ml) was added K2CO3 (2.34 g, 16.98 mmol) and benzyl bromide (1.83 g, 10.67 mmol). The mixture was heated at 70° C. for 16 hours. The solution was then cooled to room temperature and diluted with water followed by extraction with ethyl acetate. The combined organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum to provide the crude product, 2-d, as a solid (1.2 g).

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6afbb78f902c4bcc86e2da876f358fc6
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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