Sodium borohydride → (2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

HRID 1365462Notes

Reaction equation

HRID 1365462 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH:11]=[O:12])=[C:8]([CH3:13])[C:6]=2[N:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][OH:12])=[C:8]([CH3:13])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 566485822-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 78358255(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (400 mg, 1.34 mmol) in methanol at 0° C. was added sodium borohydride and. After stirring for 2 hours, the mixture was quenched with 50:50H2O:NaHCO3(sat. aq). The methanol was removed under reduced pressure to give a suspension which was filtered and washed with H2O followed by ether to give (2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol.

Workup

  1. customthe mixture was quenched with 50:50H2O
  2. customThe methanol was removed under reduced pressure
  3. customto give a suspension which
  4. filtrationwas filtered
  5. washwashed with H2O

Sources & evidence

ORD record
ord-3c6e285744b84f0594ee86c0c789969b
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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