Hydrochloric Acid → HCID 25026758, compound

HRID 1011204Notes

Reaction equation

HRID 1011204 reaction equation
Cl.O1CCOCC1.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:33]C)[N:19]2[CH2:22][CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][O:28][C:27]([CH3:32])([CH3:31])[CH2:26]2)=[C:15]([NH2:35])[N:14]=1)[CH2:9][CH2:10][CH3:11]>CO.C(Cl)Cl.CO>[NH2:35][C:15]1[N:14]=[C:13]([NH:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=[C:20]2[C:16]=1[NH:17][C:18](=[O:33])[N:19]2[CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][O:28][C:27]([CH3:32])([CH3:31])[CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57699602HCID 57699602, compound

Product 1

HCID 25026758HCID 25026758, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4M HCl in 1,4-dioxane (3 ml, 12.00 mmol) was added in one portion to a stirred solution of N2-butyl-9-[3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)propyl]-8-(methyloxy)-9H-purine-2,6-diamine (40 mg, 0.102 mmol) in methanol (3 ml) at room temperature and the mixture stirred under nitrogen overnight. The mixture was then concentrated and the residue dissolved in MeOH:DCM (1:15 ml) and loaded onto a 2 g aminopropyl SPE cartridge. The cartridge was washed with MeOH:DCM (1:1, 3 column volumes) and the desired fractions were concentrated in vacuo to give material of ca. 80% purity. This material was dissolved in DCM:MeOH (1:1), applied to a 2 g SCX column and eluted firstly with MeOH:DCM (3 column volumes) and the product then released by 2M ammonia in methanol: DCM (1:1, 3 column volumes). The solvent was removed to yield the title compound as a yellow solid (14 mg).

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue dissolved in MeOH
  3. washThe cartridge was washed with MeOH:DCM (1:1, 3 column volumes)
  4. concentrationthe desired fractions were concentrated in vacuo
  5. customto give material of ca. 80% purity
  6. washeluted firstly with MeOH
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-fb79f5d8b58c4249b0d8114a6dd6bbe9
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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