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

HRID 1534404ノート

反応式

HRID 1534404 の反応式
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]

参加物

12

反応物 8

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2a73b81a81b34ad481b09ae855becb02
出典データセット
uspto-grants-1992_02
特許番号
US05089168

反応ノート

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