Hydrochloric Acid → HCID 59126951, compound

HRID 1912306Notes

Reaction equation

HRID 1912306 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[O:21][CH2:22][CH3:23].[OH-].[NH4+:25].Cl>O>[NH2:25][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[O:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14923Ammonium HydroxideHCID 59126905HCID 59126905, compound

Product 1

HCID 59126951HCID 59126951, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethoxy-pyrimidine-4-carboxylic acid (380 mg, 1.1 mmol) was slurried in water (3.5 mL) and 28% aqueous ammonium hydroxide solution (720 μL, 10.6 mmol) was added. The reaction mixture was sealed and heated at 80° C. for 24 h. The reaction mixture was then acidified to pH 7 via dropwise addition of concentrated hydrochloric acid, and the crude product transferred into a 500 mL separatory funnel containing 100 mL 0.1M hydrochloric acid solution. The product was then extracted with dichloromethane five times. The combined organic layers were then dried, filtered and concentrated to yield the title compound (250 mg, 69% yield) as a tan solid: 1H NMR (DMSO-d6) δ 7.58 (dd, 1H, J=8, 9 Hz), 7.38 (dd, 1H, J=2, 9 Hz), 3.98 (q, 2H, J=7 Hz), 3.90 (d, 3H, J=1 Hz), 1.31 (t, 3H, J=7 Hz).

Workup

  1. customThe reaction mixture was sealed
  2. extractionThe product was then extracted with dichloromethane five times
  3. customThe combined organic layers were then dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3813ed7b2f704cef9e5c8af76dafdc49
Source dataset
uspto-grants-2013_12
Patent number
US08609592B2

Reaction notes

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