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

HRID 1365119Notes

Reaction equation

HRID 1365119 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+]>CO>[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)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde 10 (Example 3, General Procedure B-3, 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 material 29 required no further purification (0.9 g, 90%). MS (Q1) 286 (M)+

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. custompurification (0.9 g, 90%)

Sources & evidence

ORD record
ord-734521f0ebfa4f1dadd8b50d16635e57
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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