Acetonitrile → HCID 178498593, compound

HRID 1172054Notes

Reaction equation

HRID 1172054 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](N)[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4].C(#N)C.N([O-])=[O:26].[Na+]>OS(O)(=O)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([OH:26])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 23668193Sodium NitriteHCID 594320836-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 178498593HCID 178498593, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester (300 mg, 0.97 mmol, see U.S. Pat. No. 7,300,907 B2 for preparation) was slurried in 10 mL 1M H2SO4 plus 3 mL acetonitrile, heated to 75° C. and treated in portions with sodium nitrite (350 mg, 5 mmol) over a period of 10 minutes. After 40 minutes the mixture was cooled and the yellow precipitate was taken up in 40 mL ethyl acetate, washed with 10 mL water, washed with 10 mL brine, dried, and evaporated to give 170 mg (60% yield) 6-hydroxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester; MS m/z 312, 1H NMR (DMSO-d6): δ 7.49 (m, 3H), 3.95 (s, 3H), 3.86 (s, 3H)

Workup

  1. temperatureAfter 40 minutes the mixture was cooled
  2. washwashed with 10 mL water
  3. washwashed with 10 mL brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-db6512ff738d45b88c84c5e0dfa1d70a
Source dataset
uspto-grants-2010_11
Patent number
US07833940B2

Reaction notes

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