5-Methyl-3-pyrimidin-4-yl-isoxazole-4-carboxylic acid ethyl ester → 5-Methyl-3-pyrimidin-4-yl-isoxazole-4-carboxylic acid

HRID 332509Notes

Reaction equation

HRID 332509 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.COC(=O)C1C=CN=C(OCC2C(C3C=CC=CC=3)=NOC=2C)C=1>>[CH3:11][C:10]1[O:9][N:8]=[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)[C:6]=1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 671576055-Methyl-3-pyrimidin-4-yl-isoxazole-4-carboxylic acid ethyl esterHCID 684433292-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid methyl ester

Product 1

HCID 671578195-Methyl-3-pyrimidin-4-yl-isoxazole-4-carboxylic acidYield 74.5%

Procedure

As described for example 58b, 5-methyl-3-pyrimidin-4-yl-isoxazole-4-carboxylic acid ethyl ester (500 mg, 2.1 mmol) was converted, instead of 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid methyl ester, to the title compound (321 mg, 73%) which was obtained as an off white solid. MS: m/e=204.1 [M−H]−.

Sources & evidence

ORD record
ord-7cdb1c7fffda4d1d9cf7e1d992dba189
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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