Sodium borohydride → (2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

HRID 888913Notes

Reaction equation

HRID 888913 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=[O:12])=[CH:8][C:6]=2[N:7]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11][OH:12])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (3.2 g, 11.31 mmol) in anhydrous THF (100 mL) and IMS (70 mL) was added sodium borohydride (0.47 g, 12.42 mmol) and the resulting mixture stirred at RT for 2 h. The reaction mixture was partitioned between DCM and a sat. aqueous solution of NaHCO3. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo. The resultant residue was triturated with water gave the title compound as a white solid (2.9 g, 91%).

Workup

  1. customThe reaction mixture was partitioned between DCM
  2. customThe organic layer was isolated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was triturated with water

Sources & evidence

ORD record
ord-be4e02733702487591e08ab405933524
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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