Hydrochloric Acid → HCID 19883248, compound

HRID 846818Notes

Reaction equation

HRID 846818 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH2:29][NH:28][CH2:27][CH2:26][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[N:14]=2)=[CH:5][CH:4]=1.[CH2:30](N(CC)CC)[CH3:31].ICC.Cl.C([OH:43])C>CO>[OH2:43].[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH2:29][N:28]([CH2:30][CH3:31])[CH2:27][CH2:26][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=3)[N:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6340IodoethaneHCID 8471TriethylamineHCID 67900435HCID 67900435, compound

Product 1

HCID 19883248HCID 19883248, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-2-(4-trifluoromethylphenylamino) -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrochloride (0.70 g, 1.73 mmol), triethylamine (0.5 mL, 3.6 mmol) and iodoethane (0.14 mL, 1.73 mmol) in ethanol (20 mL) was heated to reflux overnight. The mixture was cooled to room temperature, concentrated in vacuo, and chromatographed (silica gel, 5% methanol in methylene chloride). The hydrochloride salt was prepared by adding concentrated hydrochloric acid to a solution of the free base in methanol and recrystallized from acetone to give 0.21 g (28%) of 4-(4-chlorophenyl)-6-ethyl-2-(4-trifluromethylphenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride monohydrate. m.p. 273°-275° C. MS: 433 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. customchromatographed (silica gel, 5% methanol in methylene chloride)
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-03155931a3e54fa9b6c2d177a051e816
Source dataset
uspto-grants-1992_08
Patent number
US05137890

Reaction notes

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