Water → HCID 69309517, compound

HRID 1947028Notes

Reaction equation

HRID 1947028 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([CH:18]=[O:19])[C:12]=3[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.[BH4-].[Na+].O>CO.C(Cl)Cl>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[C:13]([CH2:18][OH:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86620843HCID 86620843, compound

Product 1

HCID 69309517HCID 69309517, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-Methylsulfanyl-pyrimidin-4-yl)-1H-indole-4-carbaldehyde (14.38 g, 53.39 mmol) was suspended in a mixture of MeOH (200 mL) and DCM (100 mL), cooled in an ice bath, treated with NaBH4, and stirred for 1 h. Water was then added, and the solvents concentrated in vacuo. The residue was them partitioned between water and EtOAc, filtered, and the precipitate was triturated with ether, filtered and solvent removed in vacuo overnight to yield [1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yl]-methanol (10 g).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationthe solvents concentrated in vacuo
  3. custompartitioned between water and EtOAc
  4. filtrationfiltered
  5. customthe precipitate was triturated with ether
  6. filtrationfiltered
  7. customsolvent removed in vacuo overnight

Sources & evidence

ORD record
ord-4a8fca4c85ae4e86865bbe45e8bce866
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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