Isoamyl Nitrite → HCID 22133912, compound

HRID 1369386Notes

Reaction equation

HRID 1369386 reaction equation
CS([O-])(=O)=O.N[C:7]1[N:15]=[C:14]([C:16]#[C:17][C:18]2([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:13]=[C:12]2[C:8]=1[N:9]=[C:10]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[N:11]2[CH3:25].N(OCCC(C)C)=O>O1CCCC1>[F:32][C:28]1[CH:27]=[C:26]([C:10]2[N:11]([CH3:25])[C:12]3[C:8]([N:9]=2)=[CH:7][N:15]=[C:14]([C:16]#[C:17][C:18]2([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[N:13]=3)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 85257MethanesulfonateHCID 9842054HCID 9842054, compound

Product 1

HCID 22133912HCID 22133912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A methanesulfonate (470 mg) prepared from 1-{2-[6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethynyl}-1-cyclohexanol by a conventional method was dissolved in 25 ml of tetrahydrofuran, 0.44 ml of isoamyl nitrite was added thereto and the mixture was heated under reflux for 1 hour. The reaction solution was concentrated to dryness and purified by a silica gel column (eluting with dichloromethane:methanol=95:5) to give 20 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction solution was concentrated to dryness
  4. custompurified by a silica gel column (eluting with dichloromethane:methanol=95:5)

Sources & evidence

ORD record
ord-7b8c79a520d64813b4d47e637ff666ae
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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