Cesium carbonate → 4-[4-(4-Propylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzonitrile

HRID 1788014ノート

反応式

HRID 1788014 の反応式
N1(C2N=[C:9]([CH2:16][CH2:17][CH2:18][NH2:19])[C:10]3SC[CH2:13][C:11]=3N=2)CCNCC1.[CH2:20]([NH:23][C:24]1[C:25]2[S:47][CH2:46][CH2:45][C:26]=2[N:27]=[C:28]([N:30]2[CH2:35][CH2:34][N:33](C3C=C(C=CC=3)C(O)=O)[CH2:32][CH2:31]2)[N:29]=1)[CH2:21][CH3:22].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:20]([NH:23][C:24]1[C:25]2[S:47][CH2:46][CH2:45][C:26]=2[N:27]=[C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:10]3[CH:9]=[CH:16][C:17]([C:18]#[N:19])=[CH:13][CH:11]=3)[CH2:32][CH2:31]2)[N:29]=1)[CH2:21][CH3:22]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68438559(2-Piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamineHCID 684423243-[4-(4-Propylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzoic acid

生成物 1

HCID 684853414-[4-(4-Propylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzonitrile

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

0.150 g (0.5 mmol) of (2-piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine (VII), 0.082 g (0.45 mmol) of 4-bromobenzonitrile (VIII), 0.011 g (0.05 mmol) of palladium acetate, 0.041 g (0.07 mmol) of Xantphos, and 0.204 g (0.6 mmol) of cesium carbonate are placed in 1 mL of toluene, then stirred for 24 hours at 80° C. Then the reaction mixture is combined with water and extracted with ethyl acetate. The organic phase is washed with water, dried, and evaporated to dryness. The residue is purified by chromatography through an RP column using HPLC (column: Microsorb, RP-C18, 300 Å, 10 μm, 21.4*250 mm, eluant: acetonitrile+0.1% formic acid (A), water+0.13% formic acid (B).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography through an RP column

出典と根拠

ORDレコード
ord-bfddf97fc106413dbe180be648a2ef64
出典データセット
uspto-grants-2009_03
特許番号
US07511045B2

反応ノート

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