Sodium Carbonate → Methyl 5-bromo-2-isopropylpyrimidine-4-carboxylate

HRID 2368219Notes

Reaction equation

HRID 2368219 reaction equation
[Br:1][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][C:5]([CH:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.S(Cl)(Cl)=O.[C:18]([O-])([O-])=O.[Na+].[Na+]>CO.CCOC(C)=O>[CH3:18][O:12][C:11]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([CH:8]([CH3:9])[CH3:10])[N:4]=1)=[O:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 672998985-Bromo-2-(propan-2-yl)pyrimidine-4-carboxylic acid

Product 1

HCID 67299889Methyl 5-bromo-2-isopropylpyrimidine-4-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, cooled (0° C.) solution of 5-bromo-2-isopropyl-pyrimidine-4-carboxylic acid (3 g, 12.2 mmol) in methanol (50 ml) under an argon atmosphere was added dropwise thionyl chloride (4.37 g, 2.68 ml, 36.7 mmol). When the addition was complete, the mixture was allowed to warm to rt and stirring at rt was continued for 17 h. The orange mixture was concentrated to leave a paste which was taken up in EtOAc (50 ml)/saturated aqueous Na2CO3 solution (50 ml). The aqueous phase was extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered and concentrated to leave the product (2.98 g, 94%) as a light brown oil which was used in the next reaction step without further purification.

Workup

  1. additionWhen the addition
  2. concentrationThe orange mixture was concentrated
  3. customto leave a paste which
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5eb60c53473640b292f8377ed61fd246
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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