N,N-Dimethylaniline → (S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

HRID 1534404Notes

Reaction equation

HRID 1534404 reaction equation
Cl[C:2]1(Cl)[C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)[NH:3]1.C[C@@H](CC)CBr.C(OCC)(=O)CC(OCC)=O.C[O-].[Na+].Cl.C(OC1C=CC(C(N)=N)=CC=1)CCCCCC.OC1C(C[C@@H](C)CC)=C(O)N=C(C2C=CC(OCCCCCCC)=CC=2)N=1.CN(C)C1C=CC=CC=1.[H][H]>[Pd].C(N(CC)CC)C.CO>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[N:3]=[CH:2][C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

12

Reactant 8

HCID 949N,N-DimethylanilineHCID 7761Diethyl MalonateHCID 54641671-Bromo-2-methylbutane, (+)-HCID 10942334Sodium MethoxideHCID 12238503p-Heptyloxybenzamidine hydrochlorideHCID 178418361HCID 178418361, compoundHCID 178444044(S)-4,4-dichloro-2-(p-heptyloxy-phenyl)-5-(2-methylbutyl)-pyrimidineHCID 178444047HCID 178444047, compound

Product 1

HCID 53993226(S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 40 g of (S)-4,4-dichloro-2-(p-heptyloxy-phenyl)-5-(2-methylbutyl)-pyrimidine [obtainable by reacting (S)-2-methylbutyl bromide with diethyl malonate in the presence of sodium methanolate, followed by condensation of the resultant diethyl (S)-2-methylbutyl malonate with p-heptyloxybenzamidine hydrochloride, and reacting the resultant (S)-4,6-dihydroxy-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine with phosphoroxy trichloride and dimethylaniline], 400 ml of methanol, 40 ml of triethylamine and 20 g of Pd-C (5%) is hydrogenated at room temperature under normal pressure until the theoretical amount of hydrogen has been taken up. After filtering off the catalyst and distilling off the solvent, the residue is recrystallized from ethanol. (S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine is obtained.

Workup

  1. filtrationAfter filtering off the catalyst
  2. distillationdistilling off the solvent
  3. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-2a73b81a81b34ad481b09ae855becb02
Source dataset
uspto-grants-1992_02
Patent number
US05089168

Reaction notes

Loading…