Trimethylsilyl isocyanate → [4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-urea

HRID 629010Notes

Reaction equation

HRID 629010 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[Cl:8][C:9]1[C:14]([S:15][CH3:16])=[C:13]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:10]=1>C1COCC1>[Cl:8][C:9]1[C:14]([S:15][CH3:16])=[C:13]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:6]([NH2:5])=[O:7])=[CH:25][CH:24]=2)[N:10]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 86673495HCID 86673495, compound

Product 1

HCID 86673497[4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-ureaYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilyl isocyanate (136 mg, 5 eq.) was added to a stirred solution of 4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (80 mg, 0.237 mmol.) in THF (2.0 ml) and the mixture was reacted to reflux for 16 hrs. The reaction mixture was extracted with EA and washed with brine. The crude was purified by Chromatography (Hexane/EtOAc 1:1) to give a product 28.1 mg (31.2%).

Workup

  1. customthe mixture was reacted
  2. temperatureto reflux for 16 hrs
  3. extractionThe reaction mixture was extracted with EA
  4. washwashed with brine
  5. customThe crude was purified by Chromatography (Hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-8f3dca6440bc480696c3a6da501d985f
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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