2-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonate → 2-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine

HRID 1064307Notes

Reaction equation

HRID 1064307 reaction equation
O([CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])S(C(F)(F)F)(=O)=O.[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=2)[CH:30]=[CH:29][N:28]=1>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]([CH2:9][CH2:10][N:11]3[C:15](=[O:16])[C:14]4=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]4[C:12]3=[O:21])[CH:35]=[N:36][CH:37]=2)[CH:30]=[CH:29][N:28]=1

Participants

4

Reactant 2

HCID 118094652-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonateHCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

Product 1

HCID 222735062-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phthalimidoethyl triflate (660 mg, 2.04 mmol) was added to solution of the 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine Method 2; 1.00 g, 1.95 mmol) in DCM (5 ml) and the reaction mixture stirred for 4 hours. The solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml) was added to the residue. The mixture was stirred for 5 minutes, the volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The resulting precipitate was collected by filtration, washed with water and EtOAc and dried to give the title compound 350 mg, (40%) as a solid. NMR: 3.81-3.96 (m, 2H), 4.77-4.92 (m, 2H), 6.98 (d, 1H), 7.06 (d, 1H), 7.31 (t, 1H), 7.37 (d, 1H), 7.63-7.80 (m, 6H), 7.92 (s, 1H), 8.27 (d, 1H), 9.50 (s, 1H); m/z: 443.

Workup

  1. customThe solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml)
  2. additionwas added to the residue
  3. customthe volatiles were removed by evaporation
  4. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water and EtOAc
  7. customdried

Sources & evidence

ORD record
ord-07c2d75e86964e0281dee757f53057c8
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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