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

HRID 274203

반응식

HRID 274203 반응식
Cl[C:2]1[C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[C:6](Cl)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=2)[N: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>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([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:15][CH:16]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

12

반응물 8

HCID 949N,N-DimethylanilineHCID 7761Diethyl MalonateHCID 54641671-Bromo-2-methylbutane, (+)-HCID 10942334Sodium MethoxideHCID 12238503p-Heptyloxybenzamidine hydrochlorideHCID 86743091(S)-4,6-dichloro-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidineHCID 178418361HCID 178418361, 화합물HCID 178444047HCID 178444047, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8471Triethylamine용매

실험 절차

A mixture of 40 g of (S)-4,6-dichloro-2-(p-heptyloxyphenyl)-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.

후처리

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

출처 및 근거

ORD 기록
ord-2b533768100c4e4dae509e76e64796f8
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389290

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