Benzyl Alcohol → HCID 44197794, compound

HRID 1970946Notes

Reaction equation

HRID 1970946 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)[CH:27]=2)[N:19]=[C:18]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[N:17]=1>CN(C=O)C>[CH2:7]([O:14][C:16]1[CH:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)[CH:27]=2)[N:19]=[C:18]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[N:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 23665647Potassium tert-butoxideHCID 86647917HCID 86647917, compound

Product 1

HCID 44197794HCID 44197794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of potassium tert-butoxide (2 eq, 18.6 mg) in DMF (1 ml) is added benzyl alcohol (2 eq, 7.2 μl) under an inert atmosphere of argon. After stirring at RT for 15 minutes, the mixture is treated dropwise with a solution of 4-chloro-6-[5-(3-methoxy-phenyl)-pyridin-3-yl]-2-pyridin-2-yl-pyrimidine (1 eq, 31 mg) and then allowed to stir at RT for 5 hours. The reaction is quenched with water (4 ml) and the mixture is extracted with EtOAc. The organic extracts are combined, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is loaded onto a SCX-2 cartridge (1 g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and dried under vacuum overnight to afford the title compound [M+H]+=447 as an oil.

Workup

  1. stirringto stir at RT for 5 hours
  2. customThe reaction is quenched with water (4 ml)
  3. extractionthe mixture is extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. washeluting with MeOH
  8. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-0ac581ddd00743c8bc5ddcd31c34e9af
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

Loading…