Sodium Methoxide → HCID 54474138, compound

HRID 2050421Notes

Reaction equation

HRID 2050421 reaction equation
CO[CH:3]=[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][CH3:13])[CH:5]=O.Cl.[CH:16]([O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[NH:25])=[CH:22][CH:21]=1)([CH3:18])[CH3:17].C[O-].[Na+]>CO>[CH:16]([O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]2[N:26]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][CH3:13])=[CH:5][N:25]=2)=[CH:22][CH:21]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 14400648HCID 14400648, compoundHCID 53736175HCID 53736175, compound

Product 1

HCID 54474138HCID 54474138, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 23 g of (S)-2-(methoxymethylidene)-7-methylnonanal, 26.2 g of 4-isopropoxybenzamidine hydrochloride and 250 ml of absolute methanol was treated dropwise at 10° C. with 80 ml of a 5% solution of sodium methylate in methanol. The reaction mixture was stirred at room temperature overnight and subsequently made acid (pH 4-5) with concentrated hydrochloric acid, filtered and the filtrate was concentrated. The residue was taken up in 500 ml of dichloromethane, washed several times with water, dried over sodium sulphate and concentrated. Chromatography of the residue on silica gel with hexanethyl acetate (vol. 19:1) and recrystallization from methanol gave 22.2 g of (S)-2-(4-isopropoxyphenyl)-5-(5-methylheptyl)pyrimidine; m.p. 47.2°-47.7° C.

Workup

  1. filtrationsubsequently made acid (pH 4-5) with concentrated hydrochloric acid, filtered
  2. concentrationthe filtrate was concentrated
  3. washwashed several times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customChromatography of the residue on silica gel with hexanethyl acetate (vol. 19:1) and recrystallization from methanol

Sources & evidence

ORD record
ord-7ca45c820e204087981681899d2bd8dd
Source dataset
uspto-grants-1991_05
Patent number
US05013476

Reaction notes

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