Potassium Carbonate → HCID 53482315, compound

HRID 2036633Notes

Reaction equation

HRID 2036633 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[NH:17][C:16]3[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH3:12])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:14]([CH2:37][C:36]3[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=3)[C:15]3[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[C:16]=3[N:17]=2)[CH3:12])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 178461969HCID 178461969, compound

Product 1

HCID 53482315HCID 53482315, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-amino-6-(((1S)-1-(7-(methylsulfonyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile (36 mg, 0.10 mmol), potassium carbonate (21 mg, 0.15 mmol) and 4-fluorobenzyl bromide (15 μL, 0.12 mmol) in DMF (3 mL) was stirred at rt in a sealed flask for 18 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by flash chromatography over silica gel, using 2.5% MeOH in DCM as eluent gave 4-amino-6-(((1S)-1-(1-(4-fluorobenzyl)-4-(methylsulfonyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile: 1H NMR (400 MHz, CDCl3) δ 8.08 (1H, s), 7.88 (1H, d, J=8.0 Hz), 7.44 (1H, d, J=8.0 Hz), 7.31 (1H, t, J=8.0 Hz), 6.93 (4H, t, J=8.0 Hz), 6.19 (1H, t, J=8.0 Hz), 5.80-5.71 (1H, m), 5.52 (1H, d, J=16.0 Hz), 5.50 (1H, d, J=16.0 Hz), 5.31 (2H, br), 3.47 (3H, s), 1.62 (3H, d, J=8.0 Hz); LC-MS (ESI) m/z 466.0 [M+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by flash chromatography over silica gel

Sources & evidence

ORD record
ord-71a6777f459648da8aebe94e94221dd4
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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