N-bromobutanimide → 7-Bromo-N-butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine

HRID 920664Notes

Reaction equation

HRID 920664 reaction equation
[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:29][C:12]1[C:10]2[N:11]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:7]=[CH:8][C:9]=2[N:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86731155N-Butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine

Product 1

HCID 867311567-Bromo-N-butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amineYield 80.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine (1.03 g, 3.61 mmol) in DMF (10 mL) was added NBS (0.71 g, 3.97 mmol) at room temperature. The resulting solution was stirred for 1 h and diluted with EtOAc. The resulting solution was washed with a sat. aq. solution of NaHCO3, H2O and brine. The EtOAc layer was dried (Na2SO4), concentrated and purified by ISCO to provide the desired product (1.05 g, 80%). 1H NMR (400 MHz, CD3OD) δ 8.46 (s, 1H), 7.68 (s, 1H), 7.52-7.42 (m, 2H), 7.32-7.21 (m, 2H), 3.44 (t, J=7.1 Hz, 2H), 1.68-1.54 (m, 2H), 1.49-1.36 (m, 2H), 0.95 (t, J=7.3 Hz, 3H); MS m/z 363.1 [M+H]+.

Workup

  1. washThe resulting solution was washed with a sat. aq. solution of NaHCO3, H2O and brine
  2. dry with materialThe EtOAc layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by ISCO

Sources & evidence

ORD record
ord-84aa5c1a19c74effa39bcd764aa35b2e
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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