Water → 1-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

HRID 12648

Reaction equation

HRID 12648 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][CH2:20][Cl:21].O>CS(C)=O>[Cl:21][CH2:20][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 813641-Bromo-4-chlorobutane

Product 1

HCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg, commercially available from Aldrich) and K2CO3 (546 mg) in dry DMSO (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chlorobutane (0.46 mL) was then added and the mixture was stirred at room temperature for 20 hours. Water was then added and the resulting mixture was extracted with EtAcO. The aqueous phase was acidified to pH 7 with aqueous 2% HCl solution and extracted with DCM. The organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a silica SPE cartridge (25 g) eluting with toluene/acetone from 95/5 to 75/25 to give the title compound as a colourless oil (250 mg).

Workup

  1. extractionthe resulting mixture was extracted with EtAcO
  2. extractionextracted with DCM
  3. washThe organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by a silica SPE cartridge (25 g)
  7. washeluting with toluene/acetone from 95/5 to 75/25

Sources & evidence

ORD record
ord-41e3223279b340a3bb76d5a9cf5a22f9
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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