1H-Purine-2,6-dione, 3,7-dihydro-1,3-dipropyl-8-(3-thienyl)- → HCID 14154542, compound

HRID 845038Notes

Reaction equation

HRID 845038 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([C:15]3[CH:19]=[CH:18][S:17][CH:16]=3)=[N:9][C:8]=2[N:7]([CH2:20][CH2:21][CH3:22])[C:5]1=[O:6])[CH2:2][CH3:3]>C1COCC1>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH:15]3[CH2:19][CH2:18][S:17][CH2:16]3)=[N:9][C:8]=2[N:7]([CH2:20][CH2:21][CH3:22])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 99050821H-Purine-2,6-dione, 3,7-dihydro-1,3-dipropyl-8-(3-thienyl)-

Product 1

HCID 14154542HCID 14154542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 1,3-dipropyl-8-(3-tetrahydrothienyl)xanthine is prepared as follows: To 1.1 g 1,3-dipropyl-8-(3-thienyl)xanthine in 50 ml THF is added 0.2 g 10% Pd/Al2O3, and the mixture reduced under a hydrogen atmosphere of 1000 lbs at 200° C. overnight. The reaction mixture is filtered, and the filtrate concentrated to give 0.55 g tan powder. Recrystallization from MeOH/CH2Cl2 gives 0.12 g crystals which are identical to starting material. The filtrate is concentrated and chromatographed (20% EtOAc 80% CH2Cl2 on SiO2), to give 0.14 g product. This is determined to be a 1:2 mixture of the 1,3-dipropyl-8-(3-tetrahydrothienyl)xanthine and 1,3-dipropyl-8-(2-butyl)xanthine, mp 139°-145° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-002020b0dbc241fcbf721c52fdb460d5
Source dataset
uspto-grants-1988_07
Patent number
US04755517

Reaction notes

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