Boron tribromide → HCID 23282708, compound

HRID 369850Notes

Reaction equation

HRID 369850 reaction equation
B(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=1)[NH:9][C:10]1[C:11]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[NH:16][C:12]=2[N:13]=[CH:14][N:15]=1>C(Cl)Cl>[BrH:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=1)[NH:9][C:10]1[C:11]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[NH:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23282718HCID 23282718, compound

Product 1

HCID 23282708HCID 23282708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With the exclusion of moisture, at approximately 0° C., 6 ml of boron tribromide in 100 ml of methylene chloride are added within the course of 40 min to 2.0 g (5.7 mmol) of 4-(3-chloro-anilino)-6-(4-methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidine in 60 ml of methylene chloride. After 21 hours' stirring at RT the reaction mixture is filtered. The crude product is precipitated from the filtrate with approximately 1 liter of hexane, filtered off and washed with hexane. The residue is taken up in 0.2 liter of water and 0.6 liter of ethyl acetate and rendered neutral with 5% NaHCO3 solution. The organic phase is separated off, washed with water and brine, dried over MgSO4 and concentrated by evaporation. Crystallization from hot methanol with hexane yields the title compound; analysis calculated for C18H14N4OBrCl (+0.13 H2O): C 51.47%, H 3.36%, N 13.34%, Br 19.02%, Cl 8.44%; found: C 51.58%, H 3.32%, N 13.37%, Br 19.29%, Cl 8.46%; 1H-NMR (360 MHz, DMSO-d6): 12.85 and 10.60 (2sb, 2H), 10.5-9.5 (sb), 8.37 (s, 1H), 7.92 (s, 1H), 7.67 (d, J=8, 2H), 7.63 (d, J=8, 1H), 7.51 (dd, J=8, 1 H), 7.33 (d, J=8, 1H), 7.06 (s, 1H), 6.90 (d, J=8, 2H).

Workup

  1. filtrationis filtered
  2. customThe crude product is precipitated from the filtrate with approximately 1 liter of hexane
  3. filtrationfiltered off
  4. washwashed with hexane
  5. customThe organic phase is separated off
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated by evaporation
  9. customCrystallization from hot methanol with hexane

Sources & evidence

ORD record
ord-5aed7d64d7c046d489b5284a2a0de426
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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