Lithium Hydroxide → 6-Methyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid

HRID 1260304Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[N:10][CH:9]=[C:8]([CH3:19])[N:7]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.C(O)C>[CH3:19][C:8]1[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]([NH:12][C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)=[N:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-Methyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid ethyl ester (300 mg, 1.15 mmol) was dissolved in a THF/ethanol (5 ml/1 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (4.7 ml, 1N aqueous solution). The reaction mixture was allowed to warms to ambient temperature and stirred at that temperature for 1 hour. The pH value was subsequently adjusted to acidic and the resulting suspension was filtrated. The precipitate was washed with water and ethyl acetate and dried to yield the product as light yellow solid (185 mg, 69%).

Workup

customwas allowed to warms to ambient temperature
filtrationwas filtrated
washThe precipitate was washed with water and ethyl acetate
customdried

Sources & evidence

ORD record: ord-a5644691a59f43d2859a0ae977941b2b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470820B2

Reaction notes

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