Ethyl Acetate → HCID 58075695, compound

HRID 2370220Notes

Reaction equation

HRID 2370220 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](N(OC)C)=[O:9])[C:5]([CH:14]=[CH2:15])=[C:4]([NH:16][CH3:17])[N:3]=1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])[C:5]([CH:14]=[CH2:15])=[C:4]([NH:16][CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 58075410HCID 58075410, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 58075695HCID 58075695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-N-methoxy-N-methyl-6-(methylamino)-5-vinylpyrimidine-4-carboxamide (136 mg) in THF (1.8 mL) at 0° C. was added phenylmagnesium bromide (1 M solution in THF, 1.3 mL)) dropwise, and the reaction mixture was stirred at 0° C. for 30 min. The reaction was worked up with EtOAc/sat. NH4Cl, and the crude product was purified by preparative TLC eluting with 40% EtOAc/Hexanes to give the title compound as a colorless oil (87 mg). LC-MS (M+H)+=274.03.

Workup

  1. customNH4Cl, and the crude product was purified by preparative TLC
  2. washeluting with 40% EtOAc/Hexanes

Sources & evidence

ORD record
ord-59279ae6d4134b3fbfd71770c90f1ace
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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