Hydrochloric Acid → 2-(6-Bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid

HRID 515256Notes

Reaction equation

HRID 515256 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[S:11][C:12]([C:15]([O:17]C)=[O:16])=[CH:13][N:14]=2)[CH:3]=1.[OH-].[Na+].Cl>O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[S:11][C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49821806Methyl 2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formate2×

Product 1

HCID 498218842-(6-Bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formate (Compound 11) (32.9 g, 0.1 mol) was added into a solution of NaOH (8.0 g, 0.2 mol) in water (250 mL) prepared in advance, and reacted by stirring at room temperature overnight. After filtration the filtrate was transferred into reaction flask and pH value was adjusted to 6-6.5 with hydrochloric acid (6N) when the temperature is controlled between 20° C. and 25° C. Grew the grain by stirring for 2 h, and then filtrated and dried to give Compound 12 (21.2 g, yield: 78.3%).

Workup

  1. customprepared in advance
  2. customreacted
  3. filtrationAfter filtration the filtrate
  4. customwas transferred into reaction flask and pH value
  5. customis controlled between 20° C. and 25° C
  6. stirringGrew the grain by stirring for 2 h
  7. filtrationfiltrated
  8. customdried

Sources & evidence

ORD record
ord-0235a1831eb142f1a0184a149de35a6a
Source dataset
uspto-grants-2015_08
Patent number
US09108954B2

Reaction notes

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