Sodium borohydride → (5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol

HRID 1692748Notes

Reaction equation

HRID 1692748 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])=[N:8][C:6]=2[N:7]=1.[BH4-].[Na+]>CO>[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]([CH2:11][OH:12])=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 576853925-Chloro-7-morpholinothiazolo[4,5-d]pyrimidine-2-carbaldehyde

Product 1

HCID 57685397(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-chloro-7-morpholinothiazolo[4,5-d]pyrimidine-2-carbaldehyde 43 (1.0 g, 3.5 mmol) in MeOH (30 mL) at 0° C. was treated with NaBH4(0.1 g, 3.5 mmol). The solution was allowed to warm to room temperature and stirred 15 min. The reaction mixture was quenched with a mixture of a saturated solution of sodium bicarbonate and water (1:1, v/v). The aqueous solution was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude (5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol 56 required no further purification.

Workup

  1. customThe reaction mixture was quenched with a mixture of a saturated solution of sodium bicarbonate and water (1:1
  2. extractionThe aqueous solution was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customno further purification

Sources & evidence

ORD record
ord-ccfc1d0e67f34d019769cbefc57e9e9a
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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