6-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione → 944058-91-7

HRID 2353625Notes

Reaction equation

HRID 2353625 reaction equation
Cl[CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.[Na+].[CH3:12][S:13]([O-:15])=[O:14]>CN(C=O)C>[CH3:12][S:13]([CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 2733271Sodium methanesulfinate

Product 1

HCID 24271767944058-91-7Yield 112.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

6-(Chloromethyl)-1H-pyrimidine-2,4-dione (175 g, 1.09 mol) was dissolved in DMF (2 L) and methanesulphinic acid sodium salt (133.5 g, 1.31 mol) was added. The reaction was heated to 125° C. for 2 hours then allowed to cool and the suspension filtered and concentrated in vacuo to give a yellow solid. The crude material was washed with water, filtered, then triturated with toluene. The solid was filtered then triturated with isohexane to leave the desired compound as a yellow solid (250 g). The material was used without further purification.

Workup

  1. temperatureto cool
  2. filtrationthe suspension filtered
  3. concentrationconcentrated in vacuo
  4. customto give a yellow solid
  5. washThe crude material was washed with water
  6. filtrationfiltered
  7. customtriturated with toluene
  8. filtrationThe solid was filtered
  9. customthen triturated with isohexane

Sources & evidence

ORD record
ord-d4661acd31964b99a8e98074d417810f
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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