Water → HCID 67529781, compound

HRID 2264610Notes

Reaction equation

HRID 2264610 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)[N:9]=[CH:8][N:7]=1)=[O:5])[CH3:2].[BH3-]C#N.[Na+].O>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)[N:9]=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 67530552HCID 67530552, compound

Product 1

HCID 67529781HCID 67529781, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6.21 g (21.9 mMol) 6-(1H-indol-5-yloxy)-pyrimidine-4-carboxylic acid ethyl ester in 70 ml acetic acid is cooled in an ice bath. Then 6.88 g (109 mMol) NaBH3CN are added and stirring is continued for 1 h. After addition of 17 ml water, the mixture is concentrated in vacuo. The resulting brown oil is re-dissolved in EtOAc and a 1:1 mixture of water and sat. NaHCO3, the aqueous layer separeted off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated to the crude title compound: MS: [M+1]+=286.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. dissolutionThe resulting brown oil is re-dissolved in EtOAc
  3. additiona 1:1 mixture of water and sat. NaHCO3
  4. extractionextracted twice with EtOAc
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to the crude title compound

Sources & evidence

ORD record
ord-cb04055590e64293ba7263c32a3cfe01
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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