Acetone → 2-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol

HRID 2093411Notes

Reaction equation

HRID 2093411 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.C([Li])CCC.[CH3:23][C:24]([CH3:26])=[O:25]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:24]([OH:25])([CH3:26])[CH3:23])[N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 715006872-Chloro-9-methyl-6-(4-morpholinyl)-9H-purineHCID 178418339Butyllithium

Product 1

HCID 580152132-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Chloro-9-methyl-9H-purin-6-yl)morpholine (233 mg) was cooled in 5 mL of anhydrous THF to −78° C. before adding 2 eq of a 2.5 M solution of n-butyl lithium. The reaction was stirred for 1 hour at −78° C. upon which 3 eq of acetone were added. The reaction was subsequently warmed to 0° C. after 30 minutes. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was concentrated to give crude 2-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol (95 mg).

Workup

  1. additionwere added
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-0b2c969c4cc448a88d3ada690381e98c
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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