6-Chlorouracil → 6-[3-(Hydroxymethyl)anilino]pyrimidine-2,4(1H,3H)-dione

HRID 2228437Notes

Reaction equation

HRID 2228437 reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:15]>COCCO>[OH:15][CH2:14][C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=1)[NH:10][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 732726-ChlorouracilHCID 802933-Aminobenzyl alcohol

Product 1

HCID 184699106-[3-(Hydroxymethyl)anilino]pyrimidine-2,4(1H,3H)-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

6-chlorouracil (1 mmol) and meta-aminobenzyl alcohol (2.0 mmol) were dissolved in 10 ml 2-methoxyethanol to form a reaction mixture. The mixture was then stirred at reflux for 10 hours to form 6-(meta-hydroxymethyl anilino)uracil with a yield of 86%. The hydroxy group was displaced by a bromo group by reacting the hydroxymethyl anilino-uracil (0.5 mmol) with 30% HBr in acetic acid (10 ml), thus forming 6-(meta-bromomethyl anilino)uracil with a yield of 90%. The bromo group was further replaced by a thiocyanate group by reacting 0.4 mmol 6-(meta-bromomethyl anilino)uracil with 2 mmol KSCN to form 6-(meta-mercaptocyanomethyl anilino)uracil (MMCMAU) with a yield of 80%. mMCMAU was then hydrolyzed to 6-(meta-thiomethyl anilino)uracil in 5 mL of 2N NaOH. The final product, 6-(meta-disulfidemethyl anilino)uracil, was formed quantitatively by reacting 6-(meta-thiomethyl anilino)uracil with methyl methane thiosulfonate in 2 molar excess.

Workup

  1. customto form a reaction mixture
  2. temperatureat reflux for 10 hours

Sources & evidence

ORD record
ord-47f1e66bff3845699552f0e633c262d6
Source dataset
uspto-grants-2002_07
Patent number
US06417180B1

Reaction notes

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