Sodium Hydroxide → HCID 58421551, compound

HRID 406070Notes

Reaction equation

HRID 406070 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[S:32][C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[O:23][CH:24]3[CH2:29][CH2:28][C:27]([F:31])([F:30])[CH2:26][CH2:25]3)[C:9]=2[C:8]=1[CH3:33])=[O:6]>C1COCC1.CO>[F:31][C:27]1([F:30])[CH2:28][CH2:29][CH:24]([O:23][C:17]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=2[NH:15][C:14]2[C:9]3[C:8]([CH3:33])=[C:7]([C:5]([OH:6])=[O:4])[S:32][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58421756HCID 58421756, compound

Product 1

HCID 58421551HCID 58421551, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.620 ml sodium hydroxide solution (2M) was added to 0.110 g 4-[2-(4,4-difluoro-cyclohexyloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (cpd. 33.1) in 4 ml THF/MeOH (1/1). An additional aliquot of sodium hydroxide solution was added when the reaction mixture was stirred at rt overnight. After further 6 hours at rt the mixture was concentrated, the resulting aq. layer was adjusted to pH 4-5 with aq. 2 M aq.HCl and stirred under cooling for 30 minutes. Then the mixture was filtered, the filtercake was washed with water and dried.

Workup

  1. concentrationAfter further 6 hours at rt the mixture was concentrated
  2. stirringHCl and stirred
  3. temperatureunder cooling for 30 minutes
  4. filtrationThen the mixture was filtered
  5. washthe filtercake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-5d4c620844654694b6607b89c5465b68
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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