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

HRID 1788014노트

반응식

HRID 1788014 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bfddf97fc106413dbe180be648a2ef64
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511045B2

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