Hydrochloric Acid → 5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-1H-pyridin-2-one

HRID 216136Notes

Reaction equation

HRID 216136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:19]=[N:20][C:21]([O:24]C)=[CH:22][CH:23]=2)[N:15]=[C:14]([S:26][CH3:27])[N:13]=1.Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:13]=[C:14]([S:26][CH3:27])[N:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][CH:19]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11553210[2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidin-4-yl]-amine

Product 1

HCID 115455985-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-1H-pyridin-2-oneYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [2-(2-chloro-6-fluoro-phenyl)-ethyl]-[6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidin-4-yl]-amine [1.5 g, 3.7 mmol, Example 30] and concentrated hydrochloric acid (5 mL) in EtOH (95%, 30 mL) is heated to 90° C. for 15 hours, and concentrated. The residue is diluted with water, and the pH of the solution is adjusted to 7. The resulting solid is filtered and dried to afford 5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-1H-pyridin-2-one [1.1 g, 76%, Example 31]. LCMS: RT=3.12 minutes, MS: 391 (M+H).

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with water
  3. filtrationThe resulting solid is filtered
  4. customdried

Sources & evidence

ORD record
ord-4f2b9ec9b6274aae8d4b2d1c2c7b7cd2
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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