Morpholine → HCID 86673505, compound

HRID 629016Notes

Reaction equation

HRID 629016 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([S:9][CH3:10])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CC(=O)OCC>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]([S:9][CH3:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2441072,4-dichloro-5-(methylsulfanyl)pyrimidine

Product 1

HCID 86673505HCID 86673505, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the 2,4-dichloro-5-(methylthio)pyrimidine (1.16 g, 6 mmole) in acetone (10 ml) at 0° C. containing Na2CO3 (1.1 eq, 6.6 mmole, 0.7 g) was treated dropwise with a solution of morpholine (1.0 eq, 6.6 mmole, 0.6 ml) in acetone (2 ml) and stirred for 1 hr at 0° C. TLC (EA:Hex=1:2, Rf=0.6) showed completion of the reaction to give two products. The acetone was removed in vacuo, the residue was partitioned between water and EA, and the organic layer was dried (MgSO4) and evaporated in vacuo. Column chromatography (EA/Hex=1/6) gave the product (700 mg, 47%).

Workup

  1. customcompletion of the reaction
  2. customto give two products
  3. customThe acetone was removed in vacuo
  4. customthe residue was partitioned between water and EA
  5. dry with materialthe organic layer was dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8c82c7cac02842708c1380b1bf947954
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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