Hydrochloric Acid → 6-Amino-2-(butylamino)-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-7,9-dihydro-8H-purin-8-one

HRID 1011173Notes

Reaction equation

HRID 1011173 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:24]C)[N:12]2[CH2:15][CH:16]2[CH2:21][CH2:20][O:19][C:18]([CH3:23])([CH3:22])[CH2:17]2)=[C:8]([NH2:26])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl>CO.O1CCOCC1>[NH2:26][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:24])[N:12]2[CH2:15][CH:16]1[CH2:21][CH2:20][O:19][C:18]([CH3:23])([CH3:22])[CH2:17]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57699692N2-Butyl-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-8-methoxy-9H-purine-2,6-diamine

Product 1

HCID 576997186-Amino-2-(butylamino)-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-7,9-dihydro-8H-purin-8-oneYield 52.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N2-butyl-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-8-methoxy-9H-purine-2,6-diamine (73 mg) in MeOH (2 mL) was treated with 4N HCl in 1,4-dioxane (1 mL) and was stirred for 4 h. The reaction was evaporated and the residue treated with water then basified with saturated sodium bicarbonate solution. The resulting solid was filtered, washed with water and dried. The solid was re-precipitated from ether/light petrol to give the title compound (37 mg).

Workup

  1. customThe reaction was evaporated
  2. additionthe residue treated with water
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe solid was re-precipitated from ether/light petrol

Sources & evidence

ORD record
ord-d6f777a6bab7490680745212478bb275
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…