Sodium Hydroxide → 2-[[(2,3-Difluorophenyl)methyl]thio]-4,6(1H,5H)-pyrimidinedione

HRID 1455003Notes

Reaction equation

HRID 1455003 reaction equation
[OH-].[Na+].[CH2:3]1[C:10](=[O:11])[NH:9][C:7](=[S:8])[NH:6][C:4]1=[O:5].[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br>C(O)C.O.C(O)C.O>[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][S:8][C:7]1[NH:6][C:4](=[O:5])[CH2:3][C:10](=[O:11])[N:9]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 2723628Thiobarbituric acid

Product 1

HCID 689050892-[[(2,3-Difluorophenyl)methyl]thio]-4,6(1H,5H)-pyrimidinedione

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (6.1 g) in ethanol (20 ml) and water (20 ml) was added to a suspension of 4,6-dihydroxy-2-thiopyrimidine in ethanol/water (120 ml/120 ml). 2,3-difluorobenzyl bromide (28.4 g) was added dropwise to this solution. The mixture was heated at 60° C. for 2 h and stirred at room temperature for 20 h. The solids were filtered and washed with water (200 ml), isopropanol (20 ml) and dried in vacuo at 40° C. for 24 h to yield the subtitle compound. Yield 31.0 g.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with water (200 ml), isopropanol (20 ml)
  3. customdried in vacuo at 40° C. for 24 h

Sources & evidence

ORD record
ord-58e8a820cad24e128ef47ef078896cfa
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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