Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate → 5-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester

HRID 1409596Notes

Reaction equation

HRID 1409596 reaction equation
[CH:1]1([CH2:7][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16](S(C)(=O)=O)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]>C1COCC1>[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

Participants

4

Reactant 2

HCID 86710287Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylateHCID 178419664HCID 178419664, compound

Product 1

HCID 867102965-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexylmethylmagnesium bromide solution (1.77 ml; 885 μM of 0.5M solution in THF) was added dropwise to a solution of 5-benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (0.26 g; 738 μM) in THF (10 ml). After stirring at room temperature for 1 h, the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The product was extracted into EtOAc, washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure to give the title product as a colourless oil (0.040 g; 70%). LCMS: m/z=367 (MH+).

Workup

  1. customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionThe product was extracted into EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7a8cd4a0789144718e3ec847629f597e
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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