Hydrochloric Acid → 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

HRID 910747Notes

Reaction equation

HRID 910747 reaction equation
C(N(CC)CC)C.[C:8]([OH:16])(=[O:15])/[C:9](=[C:11](\[CH:13]=O)/[Br:12])/Br.[CH3:17][S:18][C:19](=[NH:21])[NH2:20].Cl>O>[Br:12][C:11]1[C:9]([C:8]([OH:16])=[O:15])=[N:20][C:19]([S:18][CH3:17])=[N:21][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 51422-Methyl-2-thiopseudoureaHCID 8471TriethylamineHCID 3033972Mucobromic Acid

Product 1

HCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

At 5° C. triethylamine (16.9 ml) was added dropwise to a solution of mucobromic acid (10.31 g) and 2-methyl-isothiourea (11.13 g) in water (200 ml). After stirring at 5° C. for 3 h, the reaction mixture was allowed to warm up (room temperature) and stirring was continued for another 54 h. The reaction mixture was acidified with conc. HCl (33%). The title product was obtained by filtration. Yield: 4.1 g. MS-ESI: [M+H]+=249/251

Workup

  1. temperatureto warm up (room temperature)
  2. stirringstirring
  3. waitwas continued for another 54 h

Sources & evidence

ORD record
ord-4bb892eb722348c4aa16befb102e1c2e
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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