Hydrochloric Acid → Methyl 2-(6-chloro-2-methylpyrimidin-4-yl-amino)thiazol-5-carboxylic acid

HRID 517619

Reaction equation

HRID 517619 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][C:11]1[N:12]=[C:13]([NH2:19])[S:14][C:15]=1[C:16]([OH:18])=[O:17].[H-].[Na+].Cl>O1CCCC1.CN(C)C(=O)C>[CH3:10][C:11]1[N:12]=[C:13]([NH:19][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=2)[S:14][C:15]=1[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 118319269Methyl 2-(6-chloro-2-methylpyrimidin-4-yl-amino)thiazol-5-carboxylic acidYield 87.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

In a reaction flask, 49.49 g 4,6-dichloro-2-methylpyrimidine (0.303 mol), 40.00 g methyl 2-aminothiazol-5-carboxylic acid (0.253 mol), and 200 ml N,N-dimethylacetamide were charged, the temperature was brought to −5° C. and 18.20 g sodium hydride (0.455 mol) in 90 ml tetrahydrofuran were added dropwise and the reaction mixture was kept under these conditions for about three hours. At the end of the reaction, 250 ml of a solution of hydrochloric acid 2N were added, the temperature was brought to the room value, the formed solid was filtered and washed with water (4×200 ml) and dried in oven under vacuum at a temperature of 55° C. for about eight hours, to give 62.89 g methyl 2-(6-chloro-2-methylpyrimidin-4-yl-amino)thiazol-5-carboxylic acid.

Workup

  1. customwas brought to −5° C.
  2. additionwere added
  3. filtrationthe formed solid was filtered
  4. washwashed with water (4×200 ml)
  5. customdried in oven under vacuum at a temperature of 55° C. for about eight hours

Sources & evidence

ORD record
ord-c6b4fa359e61427087f2bde4f7340faf
Source dataset
uspto-grants-2015_08
Patent number
US09115124B1

Linked notes

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