Boron tribromide → HCID 86603372, compound

HRID 900173Notes

Reaction equation

HRID 900173 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:28][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][C@@H:22]4[CH2:25][CH2:24][C@@H:23]4[O:26]C)[C:14]=3[C:13]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:8][CH:7]=1.B(Br)(Br)Br>ClCCl>[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[NH:28][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][C@H:22]4[CH2:25][CH2:24][C@H:23]4[OH:26])[C:14]=3[C:13]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86603373HCID 86603373, compound

Product 1

HCID 86603372HCID 86603372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 34 mg (0.07 mmol) of trans/cis-{6-[4-(2-dimethylamino-ethoxy)-phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-(2-methoxy-cyclobutylmethyl)-amine (Example 35, Step B) in 5 ml dichloromethane was cooled to −78° C. and treated with 80 μl (0.08 mmol) of 1 M solution of BBr3 in dichloromethane. The orange slurry was stirred at −78° C. for 6.5 h, and then was warmed to 0° C. for 20 min. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (5 ml) and stirred overnight. Water was added and the mixture was extracted with dichloromethane (3×). The combined organic layers were dried over Na2SO4, filtered and purified by chromatography on silica gel (CH2Cl2:MeOH, 4:1 grading to CH2Cl2:MeOH, 1:1) to give the title compound. 1H-NMR (CD3OD) δ 0.91-0.99 (m, 1 H), 1.52-1.71 (m, 2 H), 2.03-2.10 (m, 1 H), 2.14-2.24 (m, 1 H), 2.39 (s, 6 H), 2.81 (t, J=4.0 Hz, 2 H), 3.50-3.57 (m, 1 H), 3.61-3.70 (m, 2 H), 4.10 (t, J=4.4 Hz, 2 H), 6.86 (d, J=6.8 Hz, 2 H), 7.27 (d, J=6.8 Hz, 2 H), 7.40 (d, J=6.0 Hz, 2 H), 7.42-7.51 (m, 3 H), 8.16 (s, 1 H). Mass Spectrum (ESI) m/e=458.2 (M+1).

Workup

  1. temperaturewas warmed to 0° C. for 20 min
  2. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate (5 ml)
  3. stirringstirred overnight
  4. additionWater was added
  5. extractionthe mixture was extracted with dichloromethane (3×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. custompurified by chromatography on silica gel (CH2Cl2:MeOH, 4:1 grading to CH2Cl2:MeOH, 1:1)

Sources & evidence

ORD record
ord-2b5b327dba3943d2a23197d854495db3
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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