Triethylamine → 2-(trans-2-Hydroxycyclopentylamino)-1-methyl-7-cyclopentylpurin-6-one

HRID 275327Notes

Reaction equation

HRID 275327 reaction equation
Br[C:2]1[N:3]([CH3:17])[C:4](=[O:16])[C:5]2[N:6]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:7]=[N:8][C:9]=2[N:10]=1.ClC1N(C)C(=O)C2N(C3CCCC3)C=NC=2N=1.[NH2:35][C@@H:36]1[CH2:40][CH2:39][CH2:38][C@H:37]1[OH:41].C(N(CC)CC)C>CC#N>[OH:41][C@@H:37]1[CH2:38][CH2:39][CH2:40][C@H:36]1[NH:35][C:2]1[N:3]([CH3:17])[C:4](=[O:16])[C:5]2[N:6]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:7]=[N:8][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-olHCID 200877782-Bromo-1-methyl-7-cyclopentylpurin-6-oneHCID 200878272-Chloro-1-methyl-7-cyclopentylpurin-6-one

Product 1

HCID 537372702-(trans-2-Hydroxycyclopentylamino)-1-methyl-7-cyclopentylpurin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-1-methyl-7-cyclopentylpurin-6-one and 2-chloro-1-methyl-7-cyclopentylpurin-6-one (11.4 g), (±) trans-2-aminocyclopentanol (1.2 g, 11 mmol), and triethylamine (1.2 ml) in CH3CN (20 ml) is heated to reflux for 12 hr. The resultant mixture is cooled, concentrated in vacuo, and partitioned between EtOAc/THF 1:1 and brine. The organic layers are concentrated in vacuo and the residue is purified by flash chromatography using 6% EtOH in CH2Cl2 to give 2-(trans-2-hydroxycyclopentylamino)-1-methyl-7-cyclopentylpurin-6-one, a colorless solid (1.4 gm, MS FAB: M+H=318). A mixture of 2-(trans-2-hydroxycyclopentylamino)-1-methyl-7-cyclopentylpurin-6-one (1.3 gm, 4.1 mm) and triphenylphosphine dibromide (prepared from triphenylphosphine (1.2 g) and 0.2 ml bromine) in DMF (20 ml) is stirred at room temperature for 18 hr and heated to 70° C. for 6 hr. Dilute NaOH is added to the cooled reaction mixture to adjust the pH to 10, and the resultant solution is extracted with EtOAC/THF (1:1). The organic layer is concentrated in vacuo and purified by flash chromatography using 15% EtOH in CH2Cl2 and recrystallized from CH2Cl2 /hexane to give the title compound, a solid, mp 133°-134° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 12 hr
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc/THF 1:1 and brine
  5. concentrationThe organic layers are concentrated in vacuo
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-65af581e679d4851b98706f728936d4e
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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