Thymine → HCID 59337581, compound

HRID 1661071Notes

Reaction equation

HRID 1661071 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][CH2:21][Cl:22].C(Cl)Cl>CN(C=O)C>[Cl:22][CH2:21][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 1135ThymineHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 59337581HCID 59337581, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-methyl-2,4(1H,3H)-pyrimidinedione (commercially available, 0.55 g, 3.97 mmol) was dissolved in dry DMF (15 mL). K2CO3 (0.548 g, 3.97 mmol) was added and the mixture stirred at room temperature for 1 hour. 1-bromo-5-chloropentane (0.526 ml, 3.97 mmol) was then added and the suspension was stirred at room temperature for 4 h. The volume of solvent was reduced, then DCM was added and the organic layer was washed with water, the organic phase was evaporated and the crude purified by FC (DCM/MeOH 98/2-95/5) to afford 0.1 g of the title compound (y=11%).

Workup

  1. stirringthe suspension was stirred at room temperature for 4 h
  2. washthe organic layer was washed with water
  3. customthe organic phase was evaporated
  4. customthe crude purified by FC (DCM/MeOH 98/2-95/5)

Sources & evidence

ORD record
ord-f8f2f4ff8124416b8daf0431c97f5d1f
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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