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

HRID 1111732

반응식

HRID 1111732 반응식
[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

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178508668HCID 178508668, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-747b7299fb254dae8b90aad54077792c
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04118561

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