Sodium borohydride → HCID 58439142, compound

HRID 1922994Notes

Reaction equation

HRID 1922994 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:13]=[O:14])[N:8]2[CH2:11][CH3:12])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:13][OH:14])[N:8]2[CH2:11][CH3:12])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58439184HCID 58439184, compound

Product 1

HCID 58439142HCID 58439142, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-9-ethyl-6-morpholino-9H-purine-8-carbaldehyde (2.4 g) in MeOH (200 mL) at 0° C. was treated portion wise with sodium borohydride (0.84 g). The reaction was warmed to room temperature and stirred 15 minutes. The reaction mixture was quenched with saturated solution of sodium bicarbonate. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to yield crude (2-chloro-9-ethyl-6-morpholino-9H-purin-8-yl)methanol (2.3 g) as a white solid.

Workup

  1. customThe reaction mixture was quenched with saturated solution of sodium bicarbonate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2453627ffa3e4fed984fe7601117599a
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…