Morpholine → HCID 68274486, compound

HRID 629029Notes

Reaction equation

HRID 629029 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[NH4+].[Cl-]>ClCCl>[CH3:9][O:8][C:7]1[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 86673510HCID 86673510, compound

Product 1

HCID 68274486HCID 68274486, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-chloro-5-methoxy-2-(4-nitro-phenyl)-pyrimidine (1.50 g, 1.0 eq) was stirred in dichloromethane (10 mL) and a solution of morpholine (0.75 mL, 1.5 eq) in dichloromethane (5 mL) was added dropwise to the mixture at 0° C. After stirring, the resulting solution was reacted overnight at r.t., NH4Cl (aq) was added to the solution and the solution was extracted with dichloromethane. The combined organic layers were washed with brine, dried and evaporated in vacuo. A product was obtained as a white solid (0.73 g, 41%).

Workup

  1. customthe resulting solution was reacted overnight at r.t.
  2. extractionthe solution was extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-af34730808814d3d8f06f9f176836bbc
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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