Ethyl Acetate → HCID 58075838, compound

HRID 2370221Notes

Reaction equation

HRID 2370221 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[C:5]([CH:16]=[CH2:17])=[C:4]([NH:18][CH3:19])[N:3]=1.[CH2:20]([Mg]Br)[CH:21]=[CH2:22].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([OH:9])[CH2:22][CH:21]=[CH2:20])[C:5]([CH:16]=[CH2:17])=[C:4]([NH:18][CH3:19])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 58075695HCID 58075695, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 58075838HCID 58075838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-chloro-6-(methylamino)-5-vinylpyrimidin-4-yl)(phenyl)methanone (142 mg) in THF (2.6 mL) at rt was added allylmagnesium bromide (1.0 M solution in THF, 1.1 mL) dropwise, and the reaction mixture was stirred at rt for 30 min. The reaction was worked up with EtOAc/sat. NH4Cl, and the crude product was purified by prep. TLC eluting with 30% EtOAc/Hexanes to give the title compound as a colorless oil (133 mg). LC-MS (M−H2O+H)+=298.18.

Workup

  1. customNH4Cl, and the crude product was purified by prep

Sources & evidence

ORD record
ord-a89137bf4f2f46028cf3d29b8cf1a1ef
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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