Toluene → HCID 18948846, compound

HRID 1768557Notes

Reaction equation

HRID 1768557 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][NH2:13].Cl[C:15]1[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[N:18]=[CH:17][N:16]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1>CCOCC.O>[Cl:21][C:20]1[C:15]([NH:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[N:16][CH:17]=[N:18][C:19]=1[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 37843782-(2-Naphthyl)ethyl-amineHCID 111376684,5-Dichloro-6-ethylpyrimidine

Product 1

HCID 18948846HCID 18948846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The product of Step A (0.68 g, 4.0 mmole) and 4,5-dichloro-6-ethylpyrimidine (0.71 g, 4.0 mmole) were dissolved in triethylamine (1.1 mL, 8.0 mmole) and toluene (7 mL) and heated to reflux for 4 hours. After cooling, the reaction mixture was treated with 20 mL of water and 30 mL of ether, partitioned, and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4), concentrated and chromatographed on silica gel with 10% ethyl acetate/hexane. The title compound was obtained as a white solid (0.77 g, 62% yield) , mp 81°-83° C.

Workup

  1. temperatureto reflux for 4 hours
  2. temperatureAfter cooling
  3. custompartitioned
  4. extractionthe aqueous phase extracted with ether
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-99bfef6e92774d26bdae3bccc28e17c6
Source dataset
uspto-grants-1995_01
Patent number
US05378708

Reaction notes

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