Water → [5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](5-methylisoxazol-3-yl)methanol

HRID 32557Notes

Reaction equation

HRID 32557 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[N:15]([CH3:16])[C:14]([C:17]([C:19]4[CH:23]=[C:22]([CH3:24])[O:21][N:20]=4)=[O:18])=[N:13][C:12]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[BH4-].[Na+].O>CO>[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[N:15]([CH3:16])[C:14]([CH:17]([C:19]4[CH:23]=[C:22]([CH3:24])[O:21][N:20]=4)[OH:18])=[N:13][C:12]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10070580HCID 10070580, compound

Product 1

HCID 10047694[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](5-methylisoxazol-3-yl)methanolYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](5-methylisoxazol-3-yl)methanone (Example 39) (6 mg) was dissolved in MeOH (2 mL), sodium borohydride (3 mg) added then stirred for 1 hour. Water (1 mL) was added, stirring continued for 20 minutes then concentrated in vacuo. The residue was diluted with water (5 mL), extracted with DCM (2×6 mL), organic extracts dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a pale yellow solid (3.6 mg, 60%); MS m/e MH+ 420.

Workup

  1. stirringstirring
  2. waitcontinued for 20 minutes
  3. concentrationthen concentrated in vacuo
  4. additionThe residue was diluted with water (5 mL)
  5. extractionextracted with DCM (2×6 mL), organic extracts
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8886abced36f49708a21d019b2e2bf49
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

Loading…