Triethylamine → HCID 67960315, compound

HRID 2362326Notes

Reaction equation

HRID 2362326 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]1[N:6]([CH2:24][C:25]2[N:34]=[C:33]([CH3:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)[C:7](=[O:23])[C:8]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:10]=[N:11][C:12]=2[N:13]=1.CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:9]2[C:8]3[C:7](=[O:23])[N:6]([CH2:24][C:25]4[N:34]=[C:33]([CH3:35])[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[C:5]4=[N:4][CH2:3][CH2:2][N:13]4[C:12]=3[N:11]=[CH:10]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67969046HCID 67969046, compound

Product 1

HCID 67960315HCID 67960315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2-hydroxyethylamino)-7-(4-methoxybenzyl)-1-((4-methylquinazolin-2-yl)methyl)-1H-purin-6(7H)-one 12 (1.68 g, 3.56 mmol) in DCM (66 ml) was added Et3N (1.50 ml, 10.7 mmol) and MsCl (0.55 ml, 7.1 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was extracted with DCM, washed with water, NaHCO3 and brine, dried (MgSO4) and concentrated. The crude product was purified by flash chromatography (MeOH/DCM) to afford 3-(4-methoxybenzyl)-5-((4-methylquinazolin-2-yl)methyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one 13. 1H NMR S 8.03 (d, J=7.81, 1H), 7.87 (d, J=7.81, 1H), 7.78 (t, J=7.03, 1H), 7.55 (t, J=7.03, 1H), 7.46 (s, 1H), 7.28 (d, J=8.59, 2H), 6.85 (d, J=8.59, 2H), 5.60 (s, 2H), 5.38 (s, 2H), 4.20 (d, J=9.37, 2H), 3.78 (d, J=9.37, 2H), 3.78 (s, 3H).

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. washwashed with water, NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-0f8326dd4cb545bd97c0469912189d70
Source dataset
uspto-grants-2014_04
Patent number
US08691832B2

Reaction notes

Loading…