Formic Acid → HCID 20025943, compound

HRID 1722976Notes

Reaction equation

HRID 1722976 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([Cl:26])=[CH:8][C:9]([F:25])=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])[CH:11]=1.C(N(CC)CC)C.[CH:34](O)=[O:35]>>[Cl:26][C:7]1[CH:8]=[C:9]([F:25])[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][NH:2][CH:34]=[O:35]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 20025989HCID 20025989, compound

Product 1

HCID 20025943HCID 20025943, compound

Procedure

A mixture of 2.0 g of 3-[5-(2-aminoethoxy)-4-chloro- 2-fluorophenyl]-1-methyl-6 -trifluoromethyl-2,4(1H.3H)pyrimidinedione hydrochloride in 20 ml of formic acid are heated to boiling temperature for 20 hours with 0.47 g of triethylamine. The reaction mixture is subsequently evaporated to dryness under reduced pressure, the residue is dissolved in ethyl acetate and extracted with water and thereafter with aqueous sodium bicarbonate solution, and the organic phase is dried over anhydrous sodium sulphate. The solution is thereafter evaporated to dryness under reduced pressure, and the resinous residue is dissolved in ethyl acetate and largely concentrated by evaporation. The residue, still in the liquid state, is treated with diethyl ether until slightly turbid and is seeded. The crystals are filtered off under suction, washed with diethyl ether and dried. There is obtained N-[2-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-1(2H)-pyrimidinyl]-4 -fluorophenoxy}-ethyl]-formamide, m.p. 128°-131° C.

Workup

  1. temperatureare heated
  2. customfor 20 hours
  3. customThe reaction mixture is subsequently evaporated to dryness under reduced pressure
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. extractionextracted with water
  6. dry with materialwith aqueous sodium bicarbonate solution, and the organic phase is dried over anhydrous sodium sulphate
  7. customThe solution is thereafter evaporated to dryness under reduced pressure
  8. dissolutionthe resinous residue is dissolved in ethyl acetate
  9. concentrationlargely concentrated by evaporation
  10. additionThe residue, still in the liquid state, is treated with diethyl ether until slightly turbid
  11. filtrationThe crystals are filtered off under suction
  12. washwashed with diethyl ether
  13. customdried

Sources & evidence

ORD record
ord-fc33b4d09fa04c2195ad041a5626ce69
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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