6-Chloro-3-methyl-1-propyl-2,4(1H,3H)-pyrimidinedione → 6-Mercapto-3-methyl-1-propyl-pyrimidine-2,4(1H,3H)-dione

HRID 900741

Reaction equation

HRID 900741 reaction equation
Cl[C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH3:12])[C:4](=[O:13])[CH:3]=1.O.[SH-:15].[Na+]>C(O)C>[SH:15][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH3:12])[C:4](=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 8169336-Chloro-3-methyl-1-propyl-2,4(1H,3H)-pyrimidinedioneHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 866227106-Mercapto-3-methyl-1-propyl-pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-chloro-3-methyl-1-propyl-pyrimidine-2,4(1H,3H)-dione (3.76 g), sodium hydrosulphide hydrate (6.0 g) and ethanol (100 ml) was stirred at room temperature for 48 h then concentrated under reduced pressure. The residue was dissolved in water (500 ml) and washed with ethyl acetate (2×100 ml). The aqueous phase was acidified with dilute hydrochloric acid, then extracted with ethyl acetate (3×100 ml). The combined organic phase was dried (MgSO4) and concentrated in vacuo to give a pale yellow solid which was used directly in the next step.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (500 ml)
  3. washwashed with ethyl acetate (2×100 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow solid which

Sources & evidence

ORD record
ord-568deac23f4248b48d9e5e90da645807
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Linked notes

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