Diethylamine → HCID 22048110, compound

HRID 1759750Notes

Reaction equation

HRID 1759750 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].CS(Cl)(=O)=O.[NH:13]([C:20]1[C:25]([Br:26])=[CH:24][N:23]=[C:22]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][O:35]CCO)=[CH:30][CH:29]=2)[N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(NCC)C>C(Cl)Cl>[NH:13]([C:20]1[C:25]([Br:26])=[CH:24][N:23]=[C:22]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][O:35][CH2:2][CH2:1][N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])=[CH:32][CH:33]=2)[N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22048115HCID 22048115, compound

Product 1

HCID 22048110HCID 22048110, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (33 ml, 0.241 mmol) and methanesulphonyl chloride (19 ml, 0.241 mmol) were added to a solution of 4-anilino-5-bromo-2-[4-(2-hydroxyethoxy)methylanilino]pyrimidine (Example 31; 100 mg, 0.241 mmol) in DCM (5 ml) at 0° C. The solution was warmed to ambient temperature and left to stand for 1 hour. Diethylamine (2 ml) was added, and the mixture was heated at 50° C. for 3 hours. The solvent was removed by evaporation, and the residue was purified by column chromatography, eluting with 0-2% methanol solution in DCM containing 0.5% aqueous ammonia solution, to give the product as a cream solid (38 mg, 34%). NMR (CDCl3): 1.03 (t, 6H), 2.58 (q, 4H), 2.69 (t, 2H), 3.54 (t, 2H), 4.48 (s, 2H), 7.06 (d, 2H), 7.17 (t, 1H), 7.22 (s, 1H), 7.26 (s, 1H), 7.38 (dd, 2H), 7.49 (d, 2H), 7.58 (d, 2H), 8.15 (s, 1H); MS (MH+): 470.4, 472.4.

Workup

  1. waitleft
  2. temperaturethe mixture was heated at 50° C. for 3 hours
  3. customThe solvent was removed by evaporation
  4. customthe residue was purified by column chromatography
  5. washeluting with 0-2% methanol solution in DCM containing 0.5% aqueous ammonia solution

Sources & evidence

ORD record
ord-d6aba9ec950c425993548107dc892c67
Source dataset
uspto-grants-2005_01
Patent number
US06838464B2

Reaction notes

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