Dimethylamine → HCID 23033935, compound

HRID 1393355Notes

Reaction equation

HRID 1393355 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.CS[C:14]1[N:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][N:15]=1.[CH3:32][NH:33][CH3:34].O>O1CCCC1>[CH3:32][N:33]([CH3:34])[C:14]1[N:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23033878HCID 23033878, compound

Product 1

HCID 23033935HCID 23033935, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

77% m-Chloroperbenzoic acid (476 mg, 2.12 mmol) was added to a suspension of methyl ester of 2-(2-methylthiopyrimidin-5-yl)benzoxazole-7-carboxylic acid (400 mg, 1.33 mmol) in tetrahydrofuran (10 ml) under ice cooling and the mixture was stirred for 15 min. and then at room temperature for 3 hrs. To the reaction mixture was added dropwise 50% aqueous solution of dimethylamine at room temperature and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and water (25 ml) was added thereto. The mixture was stirred for 15 min. and extracted with ethyl acetate. The organic layer was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=4) to give methyl ester of 2-(2-dimethylaminopyrimidin-5-yl)benzoxazole-7-carboxylic acid (328 mg, 83%) as colorless crystals.

Workup

  1. waitat room temperature for 3 hrs
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. additionwas added
  4. stirringThe mixture was stirred for 15 min.
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine in turn
  7. customdried
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=4)

Sources & evidence

ORD record
ord-33704ec4e29d496eac2836c37482cf0d
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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