Diisopropylethylamine → 2-[(S)-1-(3-aminophenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine

HRID 2300891Notes

Reaction equation

HRID 2300891 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.CS([C:24]1[N:29]=[C:28]([N:30]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[N:32]=[CH:31]2)[CH:27]=[CH:26][N:25]=1)(=O)=O>CN(C=O)C>[NH3:1].[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:24]2[N:29]=[C:28]([N:30]3[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[CH:31]3)[CH:27]=[CH:26][N:25]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 155496402-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidineHCID 40637894(S)-3-(1-aminoethyl)aniline

Product 2

HCID 222AmmoniaHCID 699621012-[(S)-1-(3-aminophenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(S)-1-(3-aminophenyl)-1-aminoethane (23.7 mg) was dissolved in DMF (1 mL), diisopropylethylamine (90 μL) was added followed by 2-methylsulfonyl-4-[benzimidazol-1-yl]pyrimidine (43.2 mg). The resulting mixture was left heating at 100° C. for 65 h then cooled, concentrated in vacuo then the residue purified on silica gel twice (3% then 2% (2M NH3 in MeOH)/CH2Cl2) to yield 27.9 mg of the title compound (98%). 1H NMR (500 MHz, CDCl3, partial): δ 8.52 (br s, 1H); 8.39 (d, J=5.3 Hz, 1H); 7.83 (m, 1H); 7.36 (m, 2H); 7.18 (t, J=7.8 Hz, 1H); 6.84 (d, J=7.8 Hz, 1H); 6.77 (m, 2H); 6.61 (m, 1H); 1.61 (d, J=7.1 Hz, 3H).

Workup

  1. waitThe resulting mixture was left
  2. temperaturethen cooled
  3. concentrationconcentrated in vacuo
  4. customthe residue purified on silica gel twice (3%

Sources & evidence

ORD record
ord-6401cce149734ae8ba1d6876f1576120
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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