Water → 1-(4-chloropentyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 12651

Reaction equation

HRID 12651 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH:20]([Cl:22])[CH3:21].O>CN(C=O)C>[Cl:22][CH:20]([CH3:21])[CH2:19][CH2:18][CH2:17][N:6]1[CH:7]=[C:2]([CH3:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1135ThymineHCID 11430Potassium CarbonateHCID 154167911-Bromo-4-chloropentane

Product 1

HCID 686935801-(4-chloropentyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg) and K2CO3 (548 g) in dry DMF (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chloropentane (0.548 mL) was then added and the mixture was stirred at room temperature for 4 hours. Water was then added and the resulting mixture was extracted with dichloromethane. The aqueous phase was acidified to pH 7 with aqueous 2% HCl solution and extracted with DCM. The organic phases were dried and concentrated in vacuo. The crude product was purified by a silica SPE cartridge eluting with DCM/MeOH from 98/2 to 95/5 to give the title compound (100 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. extractionextracted with DCM
  4. customThe organic phases were dried
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by a silica SPE cartridge
  7. washeluting with DCM/MeOH from 98/2 to 95/5

Sources & evidence

ORD record
ord-37721b0f049b466395e868dac77cf5c5
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

Loading…