Hydrochloric Acid → HCID 59432074, compound

HRID 245296Notes

Reaction equation

HRID 245296 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([O:13]CC)=[CH2:12])=[C:9]([NH2:16])[N:8]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([O:24][CH3:25])[C:18]=2[F:26])[N:6]=1)=[O:4].Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11](=[O:13])[CH3:12])=[C:9]([NH2:16])[N:8]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([O:24][CH3:25])[C:18]=2[F:26])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59432123HCID 59432123, compound

Product 1

HCID 59432074HCID 59432074, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(1-ethoxy-vinyl)pyrimidine-4-carboxylic acid methyl ester (0.235 g, 0.616 mmol) was dissolved in THF (5 mL) and 2N HCl (0.616 mL, 1.231 mmol) and stirred at ambient temperature for 3 h. The reaction mixture was concentrated, triturated with water, and filtered. The product was washed with methanol and dried under vacuum to yield the title compound (0.205 g, 94% yield): 1H NMR (DMSO-d6) δ 7.7 (br s, 2H), 7.63 (dd, 1H), 7.42 (dd, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.46 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water
  3. filtrationfiltered
  4. washThe product was washed with methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3bc795584dce4ee9a17d4404a86b80b2
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

Loading…