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

HRID 1788014Notes

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

extractionextracted with ethyl acetate
washThe organic phase is washed with water
customdried
customevaporated to dryness
customThe residue is purified by chromatography through an RP column

Sources & evidence

ORD record: ord-bfddf97fc106413dbe180be648a2ef64
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511045B2

Reaction notes

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