Potassium Carbonate → tert-butyl 4-[1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

HRID 1476583ノート

反応式

HRID 1476583 の反応式
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:5]=2[C:4](=[O:17])[N:3]1[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.Cl[CH2:32][C:33]1[O:37][N:36]=[C:35]([CH2:38][O:39][CH3:40])[N:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:40][O:39][CH2:38][C:35]1[N:34]=[C:33]([CH2:32][N:7]2[C:6]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[S:10][C:5]=3[C:4](=[O:17])[N:3]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[C:2]2=[O:1])[O:37][N:36]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 252192435-(Chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazoleHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

生成物 1

HCID 67257785tert-butyl 4-[1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

According to GP1 tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (6.41 g; compound B50) is reacted with 5-(chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazole (2.44 g; compound D14) in the presence of potassium carbonate (2.07 g) in DMF (45 ml). Using WU1 a solid is obtained which is dissolved in EtOAc (400 ml) at 65° C. The solvent is removed in vacuo to a volume of 40 ml at 40° C. To this solution 20 ml of diethyl ether is added at RT and the resulting suspension is filtered off and the filter cake is washed with little amounts of EtOAc and diethyl ether. The solid is dried in vacuo at 60° C. for 1 h to give the title compound.

後処理

  1. customis obtained which
  2. customThe solvent is removed in vacuo to a volume of 40 ml at 40° C
  3. additionTo this solution 20 ml of diethyl ether is added at RT
  4. filtrationthe resulting suspension is filtered off
  5. washthe filter cake is washed with little amounts of EtOAc and diethyl ether
  6. customThe solid is dried in vacuo at 60° C. for 1 h

出典と根拠

ORDレコード
ord-80c0fdbd08854d64b6f134950335225f
出典データセット
uspto-grants-2015_04
特許番号
US09018175B2

反応ノート

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