m-Chloroperbenzoic acid → 5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-1H-pyridin-2-one

HRID 216137Notes

Reaction equation

HRID 216137 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[N:17]=[C:16](SC)[N:15]=[C:14]([C:20]2[CH:21]=[CH:22][C:23](=[O:26])[NH:24][CH:25]=2)[CH:13]=1.ClC1C=C(C=CC=1)[C:31](OO)=[O:32].C[O-].[Na+]>CO.C(Cl)Cl>[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:17]=[C:16]([O:32][CH3:31])[N:15]=[C:14]([C:20]2[CH:21]=[CH:22][C:23](=[O:26])[NH:24][CH:25]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10942334Sodium MethoxideHCID 115455985-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-1H-pyridin-2-one

Product 1

HCID 576360745-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-1H-pyridin-2-oneYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of above 5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-1H-pyridin-2-one [1 g, 2.56 mmol, Example 31] in a mixture of MeOH (30 mL) and DCM (20 mL), is added 3-chloro-peroxybenzoic acid (70%, 1.32 g, 7.68 mmol) at room temperature. After 3 hours at 20° C., a 25% solution of sodium methoxide in MeOH (12 mL) is added at 0° C. After additional 1 hour, the mixture is concentrated, diluted with water, and neutralized with 3 M hydrochloric acid (pH 7). The resulting solid is filtered, and re-dissolved in a basic solution (pH 12). After acidifying into pH 3, the precipitate is filtered, and dried to give 5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-1H-pyridin-2-one [0.92 g, 96%, Example 32] as a solid. LCMS: RT=2.23 minutes, MS: 375 (M+H).

Workup

  1. waitAfter additional 1 hour
  2. concentrationthe mixture is concentrated
  3. additiondiluted with water
  4. filtrationThe resulting solid is filtered
  5. dissolutionre-dissolved in a basic solution (pH 12)
  6. filtrationthe precipitate is filtered
  7. customdried

Sources & evidence

ORD record
ord-bf39a59eaea14cfaace7569aa4c0864c
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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