Triethylamine → HCID 20131127, compound

HRID 1903083Notes

Reaction equation

HRID 1903083 reaction equation
N[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[Cl:22][C:23]1[N:28]=[C:27](Cl)[CH:26]=[CH:25][N:24]=1.[CH2:30](N(CC)CC)C>C(O)C>[NH2:3][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:25]3[CH:26]=[CH:27][N:28]=[C:23]([Cl:22])[N:24]=3)[CH2:18][CH2:17]2)[CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 20131127HCID 20131127, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Amino-6,7-dimethoxy-2-piperazino-quinazoline (30.0 g, 0.104 mole), 2,4-dichloropyrimidine (17.3 g, 0.117 mole) and triethylamine (20.5 g, 0.203 mole) in ethanol (1200 ml) were heated at reflux for three hours. The solid which separated on cooling was filtered, slurried in hot isopropanol (500 ml), filtered and washed with hot methanol. The product was partitioned between 5% by volume methanol in methylene chloride and 10% (w/w) aqueous sodium carbonate solution, the organic layer separated, washed with water, dried (Na2SO4) and evaporated in vacuo. The resulting solid was slurried in hot isopropanol, filtered and washed with hot isopropanol to afford 20 g. of the title compound, m.p. 266° C.

Workup

  1. temperatureat reflux for three hours
  2. customThe solid which separated
  3. temperatureon cooling
  4. filtrationwas filtered
  5. filtrationfiltered
  6. washwashed with hot methanol
  7. customThe product was partitioned between 5% by volume methanol in methylene chloride and 10% (w/w) aqueous sodium carbonate solution
  8. customthe organic layer separated
  9. washwashed with water
  10. dry with materialdried (Na2SO4)
  11. customevaporated in vacuo
  12. filtrationfiltered
  13. washwashed with hot isopropanol
  14. customto afford 20 g

Sources & evidence

ORD record
ord-b4ef2555e73745f0a9470ca36a9be7a4
Source dataset
uspto-grants-1984_03
Patent number
US04435401

Reaction notes

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