2-Chloro-4-phenylpyrimidine → HCID 88714446, compound

HRID 1903080Notes

Reaction equation

HRID 1903080 reaction equation
[NH2:1][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[C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][N:24]=1>C(O)CCC>[OH2:12].[NH2:1][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:23]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)[N:3]=1.[NH2:1][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:23]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

4

Reactant 2

HCID 6053562-Chloro-4-phenylpyrimidineHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 88714446HCID 88714446, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-6,7-dimethoxy-2-piperazino-quinazoline (3.44 g, 0.012 mole) and 2-chloro-4-phenylpyrimidine (2.5 g, 0.011 mole) [J. Chem. Soc., 2328 (1951)] in n-butanol (250 ml) were heated under reflux for six hours. After cooling the solid product was collected, washed with diethylether, and partitioned between chloroform and saturated aqueous sodium carbonate solution. The chloroform layer was separated, the aqueous layer extracted with chloroform and the combined chloroform layers were washed with water, dried (Na2SO4) and evaporated in vacuo. The residue (5 g) was chromatographed on silica eluting with chloroform and chloroform-methanol (97.5:2.5 by volume). Appropriate fractions were combined, evaporated and the resulting solid crystallized from dimethylformamide (DMF)/diethyl ether to give 4-amino-6,7-dimethoxy-2-[4-(4-phenylpyrimidin-2-yl)-piperazino] quinazoline hemihydrate, (2.28 g), m.p. 250° C. (dec).

Workup

  1. temperatureunder reflux for six hours
  2. temperatureAfter cooling the solid product
  3. customwas collected
  4. washwashed with diethylether
  5. custompartitioned between chloroform and saturated aqueous sodium carbonate solution
  6. customThe chloroform layer was separated
  7. extractionthe aqueous layer extracted with chloroform
  8. washthe combined chloroform layers were washed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo
  11. customThe residue (5 g) was chromatographed on silica eluting with chloroform and chloroform-methanol (97.5:2.5 by volume)
  12. customevaporated
  13. customthe resulting solid crystallized from dimethylformamide (DMF)/diethyl ether

Sources & evidence

ORD record
ord-4ee07a7b9b174ac8a41c85ca6a978868
Source dataset
uspto-grants-1984_03
Patent number
US04435401

Reaction notes

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