Methanol → HCID 57597337, compound

HRID 1926015Notes

Reaction equation

HRID 1926015 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]3[NH:26][CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+].CO>CN(C)C=O.O>[O:1]([C:8]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]3[NH:26][CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:13][C:9]=1[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 57597298HCID 57597298, compound

Product 1

HCID 57597337HCID 57597337, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-phenoxy-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (173 mg) in N,N-dimethylformamide (5 mL) was added 1,1′-carbonyldiimidazole (97 mg) and the mixture was stirred at room temperature for 1 hr. Sodium borohydride (38 mg) was added to the reaction mixture at room temperature, and methanol (1 mL) was added dropwise. After stirring overnight at room temperature, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80) and crystallized from methanol-ethyl acetate, to give the title compound (44 mg) as a colorless powder.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80)
  7. customcrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-f8829095841b43b793a9c16f7240d96f
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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