Cesium carbonate → tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

HRID 1476627ノート

反応式

HRID 1476627 の反応式
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[NH:5][C:4]=2[CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[C:29]([O:36][CH3:37])[CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[S:10][C:9]3[C:8](=[O:11])[N:7]([CH:12]4[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]4)[C:6](=[O:25])[NH:5][C:4]=3[CH:3]=2)=[C:29]([O:36][CH3:37])[CH:28]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 67258027tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

生成物 1

HCID 67259586tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (3.00 g, compound B53), (4-fluoro-2-methoxyphenyl)boronic acid (1.30 g) and dichlorobis(tricyclohexylphosphine)palladium (257 mg) are reacted in the presence of aqueous cesium carbonate solution (5.23 ml, 2.0 M) in DME (12 ml) according to the procedure described in example B55. The reaction mixture is poured into ice-cold water and the mixture is extracted with DCM. The organic layer is washed with saturated aqueous sodium chloride solution and filtered using a phase separator. All volatile materials are removed in vacuo to yield the title compound as a solid.

後処理

  1. additionThe reaction mixture is poured into ice-cold water
  2. extractionthe mixture is extracted with DCM
  3. washThe organic layer is washed with saturated aqueous sodium chloride solution
  4. filtrationfiltered
  5. customAll volatile materials are removed in vacuo

出典と根拠

ORDレコード
ord-f939fb47fab84845acc56cbca6ab6469
出典データセット
uspto-grants-2015_04
特許番号
US09018175B2

反応ノート

読み込み中…