HCID 13060508, compound → HCID 13060564, compound

HRID 2296477Notes

Reaction equation

HRID 2296477 reaction equation
[CH3:1][CH:2]([CH:27]([CH3:30])[CH2:28][CH3:29])[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:16][CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:19](OC)=[O:20])=[O:4]>C1(OC2C=CC=CC=2)C=CC=CC=1>[O:20]=[C:19]1[N:10]2[CH:11]=[N:12][C:13]3[CH:14]=[CH:15][C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH:27]([CH3:30])[CH2:28][CH3:29])=[CH:7][C:8]=3[C:9]2=[N:16][CH:17]=[C:18]1[C:23]([O:25][CH3:26])=[O:24]

Participants

3

Reactant 1

HCID 13060508HCID 13060508, compound

Product 1

HCID 13060564HCID 13060564, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
255 °C

Procedure

A mixture of dimethyl [[6-(2,3-dimethylpentanamido)-4-quinazolinylamino]methylene]propanedioate (5.75 g) in diphenyl ether (28 ml) was stirred at 255° C. for 15 minutes and cooled to ambient temperature. The resulting solid was collected by filtration, washed with hexane, and dried. The crude crystals were chromatographed on silica gel with 4% methanol-chloroform. The product was recrystallized from a mixture of methanol and chloroform. There was obtained methyl 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (0.4 g). Concentration of the mother liquor gave a crystalline residue, which was recrystallized from a mixture of chloroform and hexane to give additional 4.25 g of the same product.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with hexane
  4. customdried
  5. customThe crude crystals were chromatographed on silica gel with 4% methanol-chloroform
  6. customThe product was recrystallized from a mixture of methanol and chloroform

Sources & evidence

ORD record
ord-661e90bf0f1840bfac50c05c72a1de26
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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