Triethylamine → 2-(trans-2-Hydroxycyclopentylamino)-1-methyl-9-cyclopentylpurin-6-one

HRID 275326Notes

Reaction equation

HRID 275326 reaction equation
Br[C:2]1[N:3]([CH3:17])[C:4](=[O:16])[C:5]2[N:6]=[CH:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[N:10]=1.ClC1N(C)C(=O)C2N=CN(C3CCCC3)C=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:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-olHCID 200877662-Chloro-1-methyl-9-cyclopentylpurin-6-oneHCID 200878232-Bromo-1-methyl-9-cyclopentylpurin-6-one

Product 1

HCID 545596842-(trans-2-Hydroxycyclopentylamino)-1-methyl-9-cyclopentylpurin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-1-methyl-9-cyclopentylpurin-6-one and 2-chloro-1-methyl-9-cyclopentylpurin-6-one (1.4 g) is mixed with (±) trans-2-aminocyclopentanol (1.2 g, 11 mmol) and triethylamine (1.2 ml) in CH3CN (20 ml) and 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-9-cyclopentylpurin-6-one, a solid (1.4 gm, MS FAB: M+H=318). The 2-(trans-2-hydroxy cyclopentylamino )-1-methyl-9-cyclopentylpurin-6-one (1.3 g, 4.1 mm), triphenylphosphine dibromide (prepared from triphenylphosphine (1.2 g) and bromine (0.2 ml)) in DMF (20 ml) is stirred at room temperature for 18 hr and heated to 70° C. for 12 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 194°-195° C.

Workup

  1. temperatureheated
  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-3069c2edc3184387b01ba2c451b1143d
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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