Toluene → HCID 86673500, compound

HRID 629012Notes

Reaction equation

HRID 629012 reaction equation
[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[N:3]=1.[Cl:23][CH2:24][CH2:25][N:26]=[C:27]=[O:28].C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:27](=[O:28])[NH:26][CH2:25][CH2:24][Cl:23])=[CH:18][CH:17]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 160352-Chloroethyl isocyanateHCID 136352318HCID 136352318, compound

Product 1

HCID 86673500HCID 86673500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenol (80.0 mg, 0.236 mmol), 1-chloro-2-isocyanato-ethane (43.1 mg, 0.354 mmol, eq=1.5), toluene and CH2Cl2 was added to the reaction vessel and flushed with argon. The reaction mixture was stirred at 80° C. for 16 hrs and then dried, and the solvent was evaporated. The reaction mixture was partitioned between EA and water, the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 2:1) to give a gray solid of 58.9 mg (58.1%)

Workup

  1. additionwas added to the reaction vessel
  2. customflushed with argon
  3. customdried
  4. customthe solvent was evaporated
  5. customThe reaction mixture was partitioned between EA and water
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 2:1)
  11. customto give a gray solid of 58.9 mg (58.1%)

Sources & evidence

ORD record
ord-d5819bf50f7e4cc9b9478192444df61a
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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