HCID 86698063, compound → HCID 86698062, compound

HRID 518905Notes

Reaction equation

HRID 518905 reaction equation
[OH:1][CH2:2][C:3]1[S:11][C:10]2[CH:9]=[N:8][C:7]([N:12](CO)[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[CH:15][C:14]=3[O:26][CH:27]([CH3:29])[CH3:28])=[N:6][C:5]=2[C:4]=1[C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[O:39][CH3:40]>C1COCC1.[OH-].[Na+]>[F:38][C:36]1[CH:35]=[CH:34][C:33]([O:39][CH3:40])=[C:32]([C:4]2[C:5]3[N:6]=[C:7]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]5)=[CH:15][C:14]=4[O:26][CH:27]([CH3:29])[CH3:28])[N:8]=[CH:9][C:10]=3[S:11][C:3]=2[CH2:2][OH:1])[CH:37]=1

Participants

4

Reactant 1

HCID 86698063HCID 86698063, compound

Product 1

HCID 86698062HCID 86698062, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 517 mg of the {[6-(hydroxymethyl)-7-(5-fluoro-2-methoxyphenyl)thieno[3,2-d]pyrimidin-2-yl][4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)phenyl]amino}methanol mixture in 24 ml of THF and 10 ml of 1M sodium hydroxide is stirred at ambient temperature for 4 h. The mixture is extracted three times with 10 ml of ethyl acetate. The organic phases are washed with 10 ml of water and the organic phases are concentrated under vacuum. The crude product is purified on 80 g of silica, elution being carried out with 5-8% of methanol in dichloromethane, so as to obtain a yellow foam. After trituration with ether, the resulting solid is filtered off and dried under vacuum, so as to obtain 247 mg of [7-(5-fluoro-2-methoxyphenyl)-2-{[4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)phenyl]amino}thieno[3,2-d]pyrimidin-6-yl]methanol in the form of a yellow solid.

Workup

  1. extractionThe mixture is extracted three times with 10 ml of ethyl acetate
  2. washThe organic phases are washed with 10 ml of water
  3. concentrationthe organic phases are concentrated under vacuum
  4. customThe crude product is purified on 80 g of silica, elution
  5. customso as to obtain a yellow foam
  6. filtrationAfter trituration with ether, the resulting solid is filtered off
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b4ca152ae5884405b55f6cb3b044feb2
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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