Chloroacetic Acid → 5,6-Dimethyluracil

HRID 63094

Reaction equation

HRID 63094 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=S)[NH:6][C:7]=1[CH3:8].ClCC(O)=[O:14]>O>[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=[O:14])[NH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 27362495,6-Dimethyl-2-thiouracil

Product 1

HCID 960315,6-DimethyluracilYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5,6-dimethyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (14.4 g, 0.09 mol, Step A) and chloroacetic acid (100.0 g, 1.06 mol) in water (43 mL) was refluxed overnight, cooled down to ambient temperature and quenched with water (500 mL). The formed precipitate was collected by filtration and dried to yield 10.3 g (79.7%) of the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.70 (s, 3H) 2.02 (s, 3H) 10.56 (s, 1H) 10.86 (s, 1H).

Workup

  1. customquenched with water (500 mL)
  2. filtrationThe formed precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1cf59a9992694d7bb67f93f1ff275d11
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

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