Morpholine → HCID 86673508, compound

HRID 629025Notes

Reaction equation

HRID 629025 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:10]([S:11][CH3:12])=[C:9](Cl)[N:8]=[C:7]([Cl:14])[N:6]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:10]([S:11][CH3:12])=[C:9]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:8]=[C:7]([Cl:14])[N:6]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86673509HCID 86673509, compound

Product 1

HCID 86673508HCID 86673508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2,6-dichloro-5-methylsulfanyl-pyrimidin-4-yl)-acetic acid methyl ester (860 mg, 3.22 mmol.), morpholine (336 mg, 3.86 mmol, 1.2 eq.) and THF (10 ml) was stirred at room temperature for 2.0 hrs. The reaction mixture was dried and the solvent was evaporated. The reaction mixture was subjected to addition of 0.1 N HCl washing free morpholine, extraction with EA and evaporation to remove the EA so as to give a crude. Purification of the crude by flash chromatography on silica gel (Hexane/EtOAc 2:1) gave a gray solid of 427 mg (42.7%).

Workup

  1. customThe reaction mixture was dried
  2. customthe solvent was evaporated
  3. additionThe reaction mixture was subjected to addition of 0.1 N HCl washing free morpholine, extraction with EA and evaporation
  4. customto remove the EA so as
  5. customto give a crude
  6. customPurification of the crude by flash chromatography on silica gel (Hexane/EtOAc 2:1)
  7. customgave a gray solid of 427 mg (42.7%)

Sources & evidence

ORD record
ord-8550ca1eaa66473d9cc3e4b7dec2543e
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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