HCID 67388691, compound → HCID 67388514, compound

HRID 905684Notes

Reaction equation

HRID 905684 reaction equation
C([O:8][C:9]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:10]=1[CH2:11][NH:12][C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[N:14]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C1COCC1.CO>[OH:8][C:9]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:10]=1[CH2:11][NH:12][C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[CH:25][CH:24]=2)[N:14]=1

Participants

5

Reactant 2

HCID 67388691HCID 67388691, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67388514HCID 67388514, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 20 ml portion of THF-methanol (2:1) mixed solution of 290 mg of 4-[(2-benzyloxy-6-fluorobenzyl)amino]-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide synthesized in the same manner as in Production Example 13 was mixed with 50 mg of 10% palladium-carbon, followed by stirring for 1 hour in a hydrogen atmosphere. The reaction mixture was filtered and then mixed with 100 mg of 10% palladium-carbon, followed by stirring for 6 hours in a hydrogen atmosphere. After filtration of the reaction mixture and subsequent evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (chloroform-methanol). By recrystallizing the resulting crude crystals (THF-methanol), 117 mg of 4-[(2-hydroxy-6-fluorobenzyl)amino]-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide was obtained as colorless crystals.

Workup

  1. customsynthesized in the same manner as in Production Example 13
  2. filtrationThe reaction mixture was filtered
  3. additionmixed with 100 mg of 10% palladium-carbon
  4. filtrationAfter filtration of the reaction mixture and subsequent evaporation of the solvent
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform-methanol)
  6. customBy recrystallizing the resulting crude crystals (THF-methanol)

Sources & evidence

ORD record
ord-a266869ac1e94a41aa10e3bbd7053733
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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