Water → HCID 23332047, compound

HRID 1706789Notes

Reaction equation

HRID 1706789 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:22]3[CH:21]=[CH:20][C:19]4[C:14](=[C:15]([NH2:24])[N:16]=[C:17]([NH2:23])[N:18]=4)[C:13]=3[CH:12]=[CH:11]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:22]3[CH:21]=[CH:20][C:19]4[C:14](=[C:15]([NH2:24])[N:16]=[C:17]([NH2:23])[N:18]=4)[C:13]=3[CH:12]=[CH:11]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23332045HCID 23332045, compound

Product 1

HCID 23332047HCID 23332047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Treat a suspension of 3.2 g. of 7-[(4-methoxyphenyl)-methyl]-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 100 ml of methylene chloride at -5° C. with 34 ml. of 0.92 M boron tribromide in methylene chloride. Keep the reaction at 20° C. for 18 hours and dilute with 100 ml. of water. Filter the resulting precipitate, stir in an aqueous potassium carbonate solution, filter, wash with water and dry. Crystallize the precipitate twice from methanol and once from dimethylformamide to obtain 0.63 g. of the title product, m.p. 292° C. (dec.), NMR (dDMSO): δ 5.33 (singlet, N--CH2 --C6H5O), 6.67 (doublet, J=9 Hz, 5H), 6.72 (doublet, J=3 Hz, 9H), 7.51 (doublet, J=3 Hz, 8H), 7.75 (doublet, J=9 Hz, 6H) p.p.m.

Workup

  1. additionTreat
  2. additiona suspension of 3.2 g
  3. customat -5° C.
  4. customthe reaction at 20° C. for 18 hours
  5. additiondilute with 100 ml
  6. filtrationFilter the resulting precipitate
  7. filtrationfilter
  8. washwash with water
  9. customdry
  10. customCrystallize the precipitate twice from methanol
  11. customonce from dimethylformamide to obtain 0.63 g

Sources & evidence

ORD record
ord-939c91f8cc8e47ffa875ef2893d9d5e9
Source dataset
uspto-grants-1980_06
Patent number
US04208520

Reaction notes

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