Tetrahydrofuran → HCID 86673498, compound

HRID 629011Notes

Reaction equation

HRID 629011 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([Cl:20])[C:17]([S:21][CH3:22])=[C:16]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:15]=2)=[CH:10][CH:9]=1)=[O:6].[OH-].[Na+].C1COCC1>O>[Cl:20][C:18]1[C:17]([S:21][CH3:22])=[C:16]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([N:7]3[CH2:2][CH2:3][NH:4][C:5]3=[O:6])=[CH:9][CH:10]=2)[N:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86673499HCID 86673499, compound

Product 1

HCID 86673498HCID 86673498, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2-chloro-ethyl)-3-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-urea (20 mg, 0.045 mmol.), 10% NaOH (0.5 ml), THF (2.0 ml), and H2O (1.0 ml) was added to a vessel. The reaction mixture was stirred at 80° C. for 8 hr and then dried, and the solvent was evaporated. The reaction mixture was partitioned between EA and 0.1N HCl, 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 3:1) to give a gray solid of 11.4 mg (62.3%).

Workup

  1. additionwas added to a vessel
  2. customdried
  3. customthe solvent was evaporated
  4. customThe reaction mixture was partitioned between EA and 0.1N HCl
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 3:1)
  10. customto give a gray solid of 11.4 mg (62.3%)

Sources & evidence

ORD record
ord-7bad5c550fd848569a5c6f9de83a3e34
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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