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

HRID 2189100Notes

Reaction equation

HRID 2189100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:22]=[CH:23][CH:24]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.CO.[OH-].[Na+:39]>C1COCC1>[Na+:39].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21](/[CH:25]=[CH:26]/[C:27]([O-:29])=[O:28])[CH:22]=[CH:23][CH:24]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25095121(2E)-3-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid

Product 1

HCID 67162242(2E)-3-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid sodium salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Initially charge 76 mg (0.164 mmol) of (2E)-3-(3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]-pyrimidin-4-yl]amino}phenyl)acrylic acid in 1.5 ml of a 1:1 mixture of methanol and THF and add 0.164 ml of 1N sodium hydroxide solution at RT. Stir the mixture at RT for 2 h, then concentrate under reduced pressure and dry the residue under high vacuum overnight. 79.6 mg (99.9% of theory) of the target compound are obtained as a yellowish solid.

Workup

  1. concentrationconcentrate under reduced pressure
  2. customdry the residue under high vacuum overnight
  3. custom79.6 mg (99.9% of theory) of the target compound are obtained as a yellowish solid

Sources & evidence

ORD record
ord-eb6148439e1c4b36aa1be2430fcfd110
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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