Sodium Hydroxide → 3-{[5,6-Bis(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid

HRID 2189089Notes

Reaction equation

C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[C:20]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1.[OH-].[Na+]>C1COCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([NH:12][C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=4)[O:5][CH2:4][C:3]([OH:38])=[O:2])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolve 107 mg (0.209 mmol) of 3-{[5,6-bis(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}-phenoxyacetic acid methyl ester in 2 ml of THF, add 0.628 ml of 1N sodium hydroxide solution at RT and stir at 50° C. for 1 h. Cool to RT and remove the THF under reduced pressure. Add water to the residue and then, with ice cooling, 1N hydrochloric acid. Filter off the precipitated solid, wash repeatedly with water and dry at 40° C. under reduced pressure. 92.5 mg (88.9% of theory) of the target compound are obtained as white solid.

Workup

temperatureCool to RT
customremove the THF under reduced pressure
filtrationFilter off the precipitated solid
washwash repeatedly with water
customdry at 40° C. under reduced pressure
custom92.5 mg (88.9% of theory) of the target compound are obtained as white solid

Sources & evidence

ORD record: ord-8978518347ac484188089f9f933c1629
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

Loading…