N-bromobutanimide → HCID 20063938, compound

HRID 359685Notes

Reaction equation

HRID 359685 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][NH:10][C:11]2[CH:16]=[C:15]([NH2:17])[N:14]=[C:13]([CH3:18])[N:12]=2)[CH:5]=[N:6][CH:7]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][C:16]1[C:11]([NH:10][NH:9][CH2:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[N:12][C:13]([CH3:18])=[N:14][C:15]=1[NH2:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20063939HCID 20063939, compound

Product 1

HCID 20063938HCID 20063938, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of N-[[(5-bromo-3-pyridinyl)methyl]amino]-2-methyl-4,6-pyrimidinediamine (1.00 g, 3.40 mmol) in carbon tetrachloride (50 mL) at 23° C. was added N-bromosuccinimide (0.61 g, 3.90 mmol). The mixture was stirred for 1.5 hours at 23° C. and then filtered. The isolated solid was purified by flash chromatography (silica gel, 1:1 EtOAc:CHCl3 then 20% MeOH in EtOAc as eluants) and two recrystallizations from methanol to provide the title compound (376 mg, 1.01 mmol, 30%): mp 221°-222° C., Rf 0.69 (20% MeOH in EtOAc); 1H NMR (DMSO-D6, 400 MHz)δ8.54 (d, J=2 Hz, 1H), 8.50 (d, J=2 Hz, 1H), 7.93 (m, 1H), 7.09 (t, J=6 Hz, 1H), 6.39 (s, 2H), 4.51 (d, J=6 Hz, 2H), 2.13 (s, 3H); IR (KBr) 3480, 3300 (NH), 2900-3150 (CH), 1650, 1600 (C=C, C=N) cm-1 ; mass spectrum m/e 375 (M+, 45%), 373 (M+, 84%), 371 (M+, 44%), 292 (C11H11BrN5, 54%), 185 (C6H6BrN2, 50%).

Workup

  1. filtrationfiltered
  2. customThe isolated solid was purified by flash chromatography (silica gel, 1:1 EtOAc
  3. customCHCl3 then 20% MeOH in EtOAc as eluants) and two recrystallizations from methanol

Sources & evidence

ORD record
ord-386ea787751645189621207141d9a8f2
Source dataset
uspto-grants-1991_03
Patent number
US05002949

Reaction notes

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