Piperazine → 1-(4-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperazin-1-yl)ethanone

HRID 1038808Notes

Reaction equation

Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:6]2[O:11][CH:10]=[CH:9][C:7]=2[N:8]=1.ClC1N=C(Cl)C2[O:27][CH:26]=[CH:25]C=2N=1.N1CCNCC1.C(Cl)(=O)C>C(Cl)Cl.CN(C=O)C>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:26](=[O:27])[CH3:25])[CH2:14][CH2:13]2)[C:6]2[O:11][CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a flask was added 2-chloro-4-(piperazin-1-yl)furo[3,2-d]pyrimidine, hydrochloride salt (0.325 g, 1.18 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [Ark Pharm] with piperazine), DMF (10 mL), TEA (0.543 mL, 3.90 mmol) and acetyl chloride (0.185 mL, 2.60 mmol). The mixture was warmed to about 35° C. and stirred overnight. The mixture was cooled to rt and diluted with DCM (50 mL). The organic layer was washed with water (50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL), dried over MgSO4, filtered, concentrated in vacuo and dried in a vacuum oven at about 40° C. to give 1-(4-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperazin-1-yl)ethanone (0.214 g, 64%): LC/MS (Table 2, Method a) Rt=1.04 min; MS m/z 281.4 (M+H)+.

Workup

customprepared
temperatureThe mixture was cooled to rt
washThe organic layer was washed with water (50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customdried in a vacuum oven at about 40° C.

Sources & evidence

ORD record: ord-859d76adcfab49d9b2485d34fdff42e8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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