Hydrochloric Acid → HCID 86633641, compound

HRID 1855528Notes

Reaction equation

HRID 1855528 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[N:3]=1.[CH2:18](OCC)[CH3:19].Cl>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:18][CH3:19])=[O:9])[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 39367491HCID 39367491, compound

Product 1

HCID 86633641HCID 86633641, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-chloro-6-(4-chloro-phenyl)-pyrimidine-4-carboxylic acid (1.35 g, 5.0 mmol) in ethanol (50 mL) was added diethyl ether (10 mL) which had been saturated previously with hydrochloric acid gas. The reaction mixture was stirred for 24 h at 20° C. The solution was evaporated under reduced pressure and the residual oil was dissolved in ethyl acetate. The solution was washed with saturated sodium hydrogencarbonate solution and with brine, dried over sodium sulfate, and evaporated under reduced pressure. The residual material was crystallized from ethyl acetate/heptane to give the title compound (1.17 g, 78%) as light yellow solid. MS ISN (m/e): 297.1 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.31 (s, 1H), 8.13 and 7.53 (2 d, 2×2H), 4.53 (q, 2H), 1.47 (t, 3H).

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residual oil was dissolved in ethyl acetate
  3. washThe solution was washed with saturated sodium hydrogencarbonate solution and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residual material was crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-15d0e174de4140a38cda732f490ddd00
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

Loading…