Dimethylformamide → 7-Benzylpyrrolo[3,2-f]quinazoline-1,3-diamine

HRID 1111732

反応式

HRID 1111732 の反応式
[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+].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)(=O)C>[C:24]1([CH2:23][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:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178508668HCID 178508668、化合物

生成物 1

HCID 4637957-Benzylpyrrolo[3,2-f]quinazoline-1,3-diamine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A suspension of 13.95 g. 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 600 ml. dry dimethylformamide is stirred under nitrogen as 3.70 g. ca. 50% sodium hydride-mineral oil dispersion is added carefully. After stirring for 1.5 hours, a solution of 9.30 g. benzyl chloride (8.5 ml.) in 20 ml. dry dimethylformamide is added during ca. 10 min. Stirring is continued for 5 hours and then 120 ml. gl. acetic acid is added to the reaction mixture. After removal of solvent (in vacuo), the residue is stirred thoroughly with excess aqueous potassium carbonate solution and filtered. The solids are collected, washed with water, and dried. The crude product is dissolved in 1.4 l. boiling methanol, treated with charcoal, and filtered through Celite. The filtrate is concentrated to ca. 125 ml. and chilled. The crystalline solid is collected, washed with acetone, and again recrystallized from methanol to afford 11.76 g. title compound, m.p. 228°, NMR (dDMSO): δ 5.53 (singlet, N-CH2C6H5), 7.12 (doublet, J-3Hz, 9H), 7.23 (doublet, 8Hz, 5 or 6H), 7.63 (doublet, J=3Hz, 8H), 7.77 (doublet, J=9Hz, 5 or 6H) p.p.m.; λmax95%EtOH 235 (ε 26,900), 260 (ε 28,620), 317 (ε 9,640), 345 sh (ε 7,520) nm; λmin95%EtOH 243 (ε 26,020), 281 (ε 2,430) nm.

後処理

  1. additionA suspension of 13.95 g
  2. stirringStirring
  3. waitis continued for 5 hours
  4. customAfter removal of solvent (in vacuo)
  5. stirringthe residue is stirred thoroughly with excess aqueous potassium carbonate solution
  6. filtrationfiltered
  7. customThe solids are collected
  8. washwashed with water
  9. customdried
  10. dissolutionThe crude product is dissolved in 1.4 l
  11. additionboiling methanol, treated with charcoal
  12. filtrationfiltered through Celite
  13. concentrationThe filtrate is concentrated to ca. 125 ml
  14. temperatureand chilled
  15. customThe crystalline solid is collected
  16. washwashed with acetone
  17. customagain recrystallized from methanol
  18. customto afford 11.76 g

出典と根拠

ORDレコード
ord-747b7299fb254dae8b90aad54077792c
出典データセット
uspto-grants-1978_10
特許番号
US04118561

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