Hydrochloric Acid → 3-Benzyl-6-mercapto-5-methyl-1H-pyrimidine-2,4-dione

HRID 1373053Notes

Reaction equation

HRID 1373053 reaction equation
[SH-:1].[Na+].[CH2:3]([N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13](Cl)[NH:12][C:11]1=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CN(C)C=O>[CH2:3]([N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([SH:1])[NH:12][C:11]1=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28015Sodium hydrosulfideHCID 189368853-benzyl-6-chloro-5-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 210740613-Benzyl-6-mercapto-5-methyl-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydrosulfide (119.8 g, 2,14 mole) was added to a cloudy solution of 3-benzyl-6-chloro-5-methyl-1H-pyrimidine-2,4-dione (178 g, 0.71 mole) in dimethylformamide (1 L) and heated to 60° C. 18 hours to give a dark green solution. The reaction solution was cooled and poured into 1 M HCl (6 L) and stirred at room temperature for 1 hour. The solid was collected by filtration and washed with water, dried under vacuum with P2O5 at 45° C. overnight to give 177.4 g. 1H-NMR (CDCl3) δ 10.45 (s, 1H), 7.41 (d, 2H), 7.23–7.30 (m, 3H), 5.07 (s, 2H), 3.59 (s, 1H), 1.96 (s, 3H).

Workup

  1. custom18 hours to give a dark green solution
  2. temperatureThe reaction solution was cooled
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. dry with materialdried under vacuum with P2O5 at 45° C. overnight
  6. customto give 177.4 g

Sources & evidence

ORD record
ord-fe28cb1577d647608f59d33300e15782
Source dataset
uspto-grants-2007_01
Patent number
US07160893B2

Reaction notes

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