Morpholine → HCID 11298128, compound

HRID 1774416Notes

Reaction equation

HRID 1774416 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8]CC=C)[C:5]([O:12][CH3:13])=[CH:4][N:3]=1.N1CCOCC1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([O:12][CH3:13])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 77230955HCID 77230955, compound

Product 1

HCID 11298128HCID 11298128, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-methoxy-4-(prop-2-en-1-yloxy)pyrimidine (95.0 g, 475 mmol) in anhydrous DCM (2 L) under nitrogen atmosphere was added morpholine (124 mL, 1.425 moL) and then Pd(Ph3P)4 (13.7 g, 11.9 mmol) and the reaction mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated until thick, then poured into EtOAc. The precipitate was collected and dried to give 52 g of a mixture of 2-chloro-5-methoxypyrimidin-4(3H)-one and morpholine (1:1). 1H-NMR (CDC3, 400 MHz) δ 7.45 (s, 1H), 3.67 (s, 3H). MS (ESI) m/z (M+H)+ 161.0.

Workup

  1. concentrationThe reaction mixture was concentrated until thick,
  2. additionthen poured into EtOAc
  3. customThe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-18ed3b9f21a24b3484253c671e10d0f5
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Reaction notes

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