Dimethylformamide → 7-(4-Pyridinyl)-7H-pyrrolo-[3,2-f]quinazoline-1,3-diamine

HRID 224688

Reaction equation

HRID 224688 reaction equation
[C:1]1([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][NH:13][C:8]=1[CH:7]=[CH:6]2.CN(C)C=O.[H-].[Na+].Cl.Br[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>C(O)(=O)C>[N:28]1[CH:29]=[CH:30][C:25]([N:13]2[C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[C:1]([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=4)[C:9]=3[CH:11]=[CH:12]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 881004-Bromopyridinium chlorideHCID 178508668HCID 178508668, compound

Product 1

HCID 233320467-(4-Pyridinyl)-7H-pyrrolo-[3,2-f]quinazoline-1,3-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 7.97 g. of 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 500 ml. of dry dimethylformamide is stirred, under nitrogen, with 4.61 g. ca. 50% sodium hydride-mineral oil dispersion for 1.5 hours. Addition of 8.95 g. of p-bromopyridine hydrochloride is followed by heating of the reaction mixture at 110° C. for 5 hours. Glacial acetic acid (10 ml) is added and the solvent is removed in vacuo. The residue is stirred thoroughly with a mixture of excess aqueous potassium carbonate solution and 100 ml. of 1 N sodium hydroxide solution, collected, washed with water and dried. Three crystallizations from methanol and one from dimethylformamide and drying afford 0.61 g. of the title product, m.p. 328.5°-329.5° C., NMR (dDMSO): δ 7.16 (doublet, J=8 Hz, 5H), 7.22 (doublet, J=3 Hz, 9H), 7.88 (doublet, J=3 Hz, 8H), 7.96 (doublet, J=8 cps, 6H) p.p.m λmax95%EtOH 255 mμ (22,900) and 297 mμ (22,100).

Workup

  1. additionAddition of 8.95 g
  2. customthe solvent is removed in vacuo
  3. customof 1 N sodium hydroxide solution, collected
  4. washwashed with water
  5. customdried
  6. customThree crystallizations from methanol and one from dimethylformamide
  7. customdrying
  8. customafford 0.61 g

Sources & evidence

ORD record
ord-eee3d3efe1a34448b96b26b73e692ec3
Source dataset
uspto-grants-1980_11
Patent number
US04233445

Linked notes

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