Methanol → HCID 23070820, compound

HRID 501384Notes

Reaction equation

HRID 501384 reaction equation
[H-].[Na+].[CH2:3]([N:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([Cl:25])=[N:11][C:10]=2[N:9]=[C:8]1[N:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]1)[C:4]#[C:5][CH3:6].[CH3:39][OH:40]>O>[ClH:25].[CH2:3]([N:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:12]([O:40][CH3:39])=[N:11][C:10]=2[N:9]=[C:8]1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:4]#[C:5][CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 23070627HCID 23070627, compound

Product 1

HCID 23070820HCID 23070820, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 mg of sodium hydride (60%; oily) was added to a mixture consisting of 7 mg of t-butyl 4-[7-(2-butynyl)-2-chloro-6-oxo-1-(2-phenylethyl)-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate and 0.5 ml of methanol. The mixture was stirred at room temperature for 20 minutes. Water was added to the reaction solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, and concentrated. 0.5 ml of trifluoroacetic acid was added to the residue. The mixture was stirred at room temperature for 30 minutes, and then concentrated. The residue was purified by reverse-phase column chromatography using 20 to 80% methanol/water (containing 0.1% concentrated hydrochloric acid) to give 4.3 mg of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationwith saturated brine, and concentrated
  4. addition0.5 ml of trifluoroacetic acid was added to the residue
  5. stirringThe mixture was stirred at room temperature for 30 minutes
  6. concentrationconcentrated
  7. customThe residue was purified by reverse-phase column chromatography

Sources & evidence

ORD record
ord-e0b495f3f4c04edcafaaa031f20bc649
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

Loading…