Potassium Hydroxide → 7-Amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylic acid

HRID 1184869Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:9]=2)[S:4][C:3]=1[C:16]([O:18]CC)=[O:17].[OH-].[K+]>C(O)C.O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:9]=2)[S:4][C:3]=1[C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of ethyl 7-amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylate 58 (100 mg, 0.346 mmol) and potassium hydroxide (97 mg, 1.728 mmol) in ethanol (5 mL) and water (1 mL) was stirred at 70° C. for 1 h. Quenched in ice cold citric acid solution. The resulting precipitate was collected, washed with water and dried to 7-amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylic acid 59 (66 mg, 73.1%). (m/z)=262 (M+H)+.

Workup

customQuenched in ice cold citric acid solution
customThe resulting precipitate was collected
washwashed with water
dry with materialdried to 7-amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylic acid 59 (66 mg, 73.1%)

Sources & evidence

ORD record: ord-de422179feba424db090c1d78d440067
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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