Hydrochloric Acid → HCID 59126950, compound

HRID 1969362Notes

Reaction equation

HRID 1969362 reaction equation
C[O:2][C:3]([C:5]1[C:10]([S:11][CH3:12])=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[NH2:13][C:9]1[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]=1[S:11][CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59126910HCID 59126910, compound

Product 1

HCID 59126950HCID 59126950, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (100 mg, 0.28 mmol) was dissolved in 2 mL methanol and 0.5 mL of 2N sodium hydroxide (1 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then acidified with a slight excess of 2N HCl. The resulting solution was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (68 mg, 70% yield): mp 153° C. (dec.): 1H NMR (CDCl3): δ 7.63 (m, 1H), 7.2 (m, 1H), 6.4 (br s, 2H), 3.98 (s, 3H), 2.42 (s, 3H).

Workup

  1. concentrationThe resulting solution was concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5912d091a72e4015a6038e3515cb3211
Source dataset
uspto-grants-2013_04
Patent number
US08426591B2

Reaction notes

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