Hydrochloric Acid → (2E)-3-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid

HRID 2189099Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6](=[O:39])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[C:17]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)=[C:23]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH:10]=1)C.Cl>C1COCC1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]2[C:17]3[C:16]([NH:15][C:11]4[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:39])=[O:5])[CH:14]=[CH:13][CH:12]=4)=[N:21][CH:20]=[N:19][C:18]=3[O:22][C:23]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Add 0.73 ml of 1N sodium hydroxide solution dropwise to a mixture of 120 mg (0.244 mmol) of (2E)-3-(3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid ethyl ester in 2 ml of THF. Stir the mixture at 50° C. overnight, then cool and acidify with 1N hydrochloric acid. Filter off the precipitated solid with suction, wash repeatedly with water and dry at 50° C. under high vacuum overnight. 106 mg (93.7% of theory) of the target compound are obtained as a colourless solid.

Workup

temperaturecool
filtrationFilter off the precipitated solid with suction
washwash repeatedly with water
customdry at 50° C. under high vacuum overnight
custom106 mg (93.7% of theory) of the target compound are obtained as a colourless solid

Sources & evidence

ORD record: ord-e4ca710d16d743f7a04d59d49654944b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

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