Phosphorus oxychloride → HCID 18973891, compound

HRID 2395060Notes

Reaction equation

HRID 2395060 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=2)[C:4](=O)[NH:3][CH:2]=1.P(Cl)(Cl)([Cl:25])=O>CN(C)C1C=CC=CC=1>[Cl:25][C:4]1[C:5]([CH2:7][CH2:8][C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=2)=[CH:6][N:1]=[CH:2][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23209856HCID 23209856, compound

Product 1

HCID 18973891HCID 18973891, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-[2-(pyrimidin-4(3 H)-on-5-yl)ethyl]benzoate (0.6 g,) was dissolved in N,N-dimethylaniline (5 ml) and treated with phosphorous-oxy-chloride (1.53 g 10 mmol). The reaction was heated to 100° C. for 2.5 hours and then evaporated at reduced pressure. The residue was diluted with EtOAc, washed (1N HCl 2×, H2O, saturated brine), dried over MgSO4 and evaporated to give tert-butyl 4-[2-(4-chloropyrimidin-5-yl)ethyl]benzoate as a brown oil (0.5 g, 64%) which was used without further purification.

Workup

  1. customevaporated at reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed (1N HCl 2×, H2O, saturated brine)
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-638b9674dac84185bd3121119a846429
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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