Potassium Carbonate → HCID 22048126, compound

HRID 1830583Notes

Reaction equation

HRID 1830583 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]([C:14]1[C:19]([Br:20])=[CH:18][N:17]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([CH3:37])[CH2:32]1>CS(C)=O>[NH:7]([C:14]1[C:19]([Br:20])=[CH:18][N:17]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][N:33]([CH3:37])[CH2:32]3)[CH:23]=2)[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1036743-(Chloromethyl)-1-methylpiperidineHCID 22048109HCID 22048109, compound

Product 1

HCID 22048126HCID 22048126, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixuture of potassium carbonate (160 mg, 1.2 mmol), 4-anilino-5-bromo-2-(3-hydroxyanilino)pyrimidine (Method 10, 200 mg, 0.6 mmol) and 3-chloromethyl-1-methylpiperidine (obtained as described in Eur. J. Med. Chem. 1994, 29, 967–73; 0.11 ml, 0.62 mmol) in DMSO (2 ml) were heated at 100° C. for 18 hours. Silica (1 g) was added and volatile material was removed by evaporation. The residue was loaded onto a Varian Mega Bond Elut column and the column was eluted with 0–10% 2.0 M methanolic ammonia solution to give the product as a brown solid (40 mg, 15%). NMR: 1.0 (m, 1H), 1.4 (m, 1H), 1.6 (m, 3H), 1.8 (m, 2H), 2.1 (s, 3H), 2.6–2.8 (m, 2H), 3.6 (m, 2H), 6.4 (d, 1H), 7.0–7.4 (m, 6H), 7.6 (m, 2H), 8.2 (s, 1H), 8.5 (s, 1H), 9.2 (s, 1H); MS (MH+): 468.5, 470.5.

Workup

  1. additionSilica (1 g) was added
  2. customvolatile material was removed by evaporation
  3. washthe column was eluted with 0–10% 2.0 M methanolic ammonia solution

Sources & evidence

ORD record
ord-d245fdf5ee194adc894938fb20325085
Source dataset
uspto-grants-2006_06
Patent number
US07067522B2

Reaction notes

Loading…