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

HRID 2267317Notes

Reaction equation

HRID 2267317 reaction equation
[C:1]([OH:9])(=[O:8])/[C:2](=[C:4](\[CH:6]=O)/[Br:5])/Br.S(O)(O)(=O)=O.[CH3:15][S:16][C:17](=[NH:19])[NH2:18].C(N(CC)CC)C.C>O>[Br:5][C:4]1[C:2]([C:1]([OH:9])=[O:8])=[N:18][C:17]([S:16][CH3:15])=[N:19][CH:6]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 752702-Methyl-2-thiopseudourea sulfateHCID 3033972Mucobromic Acid

Product 1

HCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic AcidYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mucobromic acid (58.05 g, 0.225 mol) was added to a stirred solution of 2-methyl-2-thio-pseudourea sulfate (62.66 g, 0.225 mol) in water (500 mL) at r.t. The suspension was cooled to 10° C. (ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 h. The reaction mixture was then left to stand at r.t. for 24 h. Activated carbon (Darco G-60) was added to the now dark red/brown solution and after stirring for 10 min the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the yellow precipitate was filtered off, washed with water (2×80 mL) and diethyl ether (2×100 mL), and then placed in a vacuum oven at 50° C. for 2 days to yield 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (33.13 g, 59%) as a yellow amorphous solid. 1H NMR δ (d6-DMSO, 400 MHz) 2.75 (s, 3 H), 9.20 (s, 1 H).

Workup

  1. additionwas added dropwise over 4 h
  2. waitThe reaction mixture was then left
  3. additionActivated carbon (Darco G-60) was added to the now dark red/brown solution
  4. filtrationwas filtered off
  5. filtrationthe yellow precipitate was filtered off
  6. washwashed with water (2×80 mL) and diethyl ether (2×100 mL)
  7. waitplaced in a vacuum oven at 50° C. for 2 days

Sources & evidence

ORD record
ord-1beb12e336a5485ba11a0a5f9b0b8227
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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