Hydrochloric Acid → 2-(Benzylthio)pyrimidine-4,6-diol

HRID 968217

Reaction equation

HRID 968217 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([SH:9])[N:3]=1.CN1C(=O)CCC1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>[OH-].[Na+]>[C:18]1([CH2:17][S:9][C:4]2[N:5]=[C:6]([OH:8])[CH:7]=[C:2]([OH:1])[N:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 13387N-methyl-2-pyrrolidoneHCID 178516656HCID 178516656, compound

Product 1

HCID 1785166522-(Benzylthio)pyrimidine-4,6-diol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4,6-dihydroxy-2-mercaptopyrimidine (100 g) in 5M NaOH (360 ml) was added first NMP (200 ml), then benzyl bromide (90 ml) dropwise over 2 hours. The reaction was stirred at room temperature for 24 hours, then acidified to pH 2 with conc HCl (100 ml) added dropwise over 2 hours at −5° C. to give a pink precipitate. This was isolated by decanting off the solution followed by trituration with diethyl ether (1 liter) to give the subtitled product as a white powder after filtration and drying (210 g).

Workup

  1. additionadded dropwise over 2 hours at −5° C.
  2. customto give a pink precipitate
  3. customThis was isolated
  4. customby decanting off the solution

Sources & evidence

ORD record
ord-b9207b828ca347bc84fda6ff277ac815
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Linked notes

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