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

HRID 275335Notes

Reaction equation

HRID 275335 reaction equation
Cl[C:2]1[N:3]([CH3:19])[C:4](=[O:18])[C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[N:8][C:9]=2[N:10]=1.C(N(CC)CC)C.[NH2:27][C@@H:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[OH:33]>CC#N>[OH:33][C@@H:29]1[CH2:30][CH2:31][CH2:32][C@H:28]1[NH:27][C:2]1[N:3]([CH3:19])[C:4](=[O:18])[C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[N:8][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 36530217-benzyl-2-chloro-1-methyl-1,7-dihydro-6H-purin-6-oneHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol

Product 1

HCID 105931742-(trans-2-Hydroxycyclopentylamino)-1-methyl-7-(phenylmethyl)purin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heat at reflux for 2 days a mixture of 2-chloro-1-methyl-7-(phenylmethyl)purin-6-one (3.14 g=11.4 mmol), triethylamine (1.7 g=16.8 mmol), and (±)-trans-2-aminocyclopentanol (4.04 g=39.9 mmol) in CH3CN (150 ml). Collect the precipitate, wash with water, and dry to give the title compound, a solid, FAB MS: M+1=340.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 2 days
  3. customCollect the precipitate
  4. washwash with water
  5. customdry

Sources & evidence

ORD record
ord-bfe3f2de2c344b3c935a8b5c8c02b846
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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