Boron tribromide → HCID 118162194, compound

HRID 1749414Notes

Reaction equation

HRID 1749414 reaction equation
C([O:3][CH:4]1[CH2:7][CH:6]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[C:5]1([CH3:20])[CH3:19])C.BrB(Br)Br>C(Cl)Cl>[OH:3][CH:4]1[CH2:7][CH:6]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[C:5]1([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118162129HCID 118162129, compound

Product 1

HCID 118162194HCID 118162194, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.), stirred solution of 4-((3-ethoxy-2,2-dimethylcyclobutyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (1.0 equiv.) in DCM (0.7 M) was treated with 1.0 M tribromoborane in DCM (3.0 equiv.). The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with MeOH. DCM and saturated sodium bicarbonate were added. The separated aqueous layer was extracted with DCM. The organic extract was dried over sodium sulfate, filtered and concentrated to give a brown oil, which was purified by silica gel column chromatography (0-45% ethyl acetate in hexane, 25 g column) to give (37% yield) of yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.24 (s, 1H), 5.42 (d, J=7.03 Hz, 1H), 4.09 (dt, J=7.62, 9.37 Hz, 1H), 3.80-3.89 (m, 1H), 2.77 (dt, J=7.42, 11.72 Hz, 1H), 2.48-2.54 (m, 3H), 1.84 (ddd, J=8.20, 9.47, 11.62 Hz, 1H), 1.74 (d, J=6.25 Hz, 1H), 1.23-1.28 (m, 3H), 0.99-1.03 (m, 3H). MS (ESI) m/z 264.8 [M+1]+.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with MeOH
  3. additionDCM and saturated sodium bicarbonate were added
  4. extractionThe separated aqueous layer was extracted with DCM
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil, which
  10. customwas purified by silica gel column chromatography (0-45% ethyl acetate in hexane, 25 g column)

Sources & evidence

ORD record
ord-cc33e853332049f99de10c7fcc96b2ca
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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