HCID 14151497, compound → HCID 14151498, compound

HRID 986210Notes

Reaction equation

HRID 986210 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:30]C)[C:24]=3[O:28]C)[NH:19][C:18]2=[O:32])[CH2:11][CH2:10]1>Br.C(O)(=O)C>[OH:28][C:24]1[C:23]([OH:30])=[CH:22][CH:21]=[C:20]2[C:25]=1[C:26](=[O:27])[N:17]([CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]1)[C:18](=[O:32])[NH:19]2

Participants

4

Reactant 1

HCID 14151497HCID 14151497, compound

Product 1

HCID 14151498HCID 14151498, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 3-{2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl}-5,6-dimethoxyquinazolin-2,4-(1H,3H)dione (1.6 g. 2.66M) in hydrobromic acid (48% aqueous, 9.6 ml) and glacial acetic acid (26.2 ml) was heated at reflux for 18 hours. The reaction mixture was cooled and the resulting solid was filtered, washed with ether (30 ml), hexane (30 ml) and dried under high vacuum at 62° C. overnight to give a crude product as a white solid. The crude product was recrystallized from methanol (75 ml). The product was dried under high vacuum at 62° C. for 2 days to afford 5,6-dihydroxy-3-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl quinazolin-2,4(1H,3H)-dione (dihydrobromide) as a white solid, (A): 0.72 g (yield 47.1%) mp=283°-286° C. A second crop precipitated out of the filtrate. It was filtered and dried under high vacuum at 62° C. for 6 days to afford additional 5,6-dihydroxy-3-2-[4-(2-methoxy-phenyl)-1-piperazinyl]ethyl quinazolin-2, 4(1H,3H)-dione (monohydrobromide monohydrate) as a white solid: (B) 0.54 g. yield 39.7%, mp=223°-227° C. The total yield of product was 86.8%.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting solid was filtered
  4. washwashed with ether (30 ml), hexane (30 ml)
  5. customdried under high vacuum at 62° C. overnight
  6. customto give a crude product as a white solid
  7. customThe crude product was recrystallized from methanol (75 ml)
  8. customThe product was dried under high vacuum at 62° C. for 2 days

Sources & evidence

ORD record
ord-f73cb98a01f847d09a5e76071a89e4a9
Source dataset
uspto-grants-1987_12
Patent number
US04711883

Reaction notes

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