Sodium Hydroxide → HCID 59605500, compound

HRID 1922837Notes

Reaction equation

HRID 1922837 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:17]=[C:16]4[C:12]([N:13]=[C:14]([CH:19]=[O:20])[N:15]4[CH3:18])=[C:11]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:10]=3)[C:7]3[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[OH-:31].[Na+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[CH:1]1([C:4]2[N:8]([C:9]3[N:17]=[C:16]4[C:12]([N:13]=[C:14]([C:19]([OH:31])=[O:20])[N:15]4[CH3:18])=[C:11]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:10]=3)[C:7]3[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=3[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59605221HCID 59605221, compound

Product 1

HCID 59605500HCID 59605500, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-(2-cyclopropylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (500 mg, 1.24 mmol) in EtOH (16 mL) was added AgNO3 (265 mg, 1.56 mmol) followed by a solution of NaOH (302 mg, 7.5 mmol) in H2O (5 mL). The resulting black suspension was allowed to stir at r.t. for 30 min then filtered through Celite® and the resulting filtrate concentrated in vacuo. The resulting residue was dissolved in H2O and basified by the addition of aq. NaOH. The aqueous phase was extracted with DCM then acidified to pH 2 with HCl. The aqueous phase was concentrated in vacuo to half volume then cooled on ice. The resulting precipitate was collected by filtration and dried in vacuo affording the title compound (280 mg, 55%).—1H NMR (DMSO, 400 MHz): δ 8.12-8.11 (1 H, m), 7.72-7.68 (1 H, m), 7.44-7.43 (2 H, m), 4.60 (4 H, brd s), 4.04 (3 H, s), 3.90-3.70 (4 H, m), 3.06-3.00 (1 H, m), 1.33-1.31 (4 H, m)

Workup

  1. filtrationthen filtered through Celite®
  2. concentrationthe resulting filtrate concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in H2O
  4. additionbasified by the addition of aq. NaOH
  5. extractionThe aqueous phase was extracted with DCM
  6. concentrationThe aqueous phase was concentrated in vacuo to half volume
  7. temperaturethen cooled on ice
  8. filtrationThe resulting precipitate was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-42611e6b39bf4832adfe9b127f90a904
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…