Water → HCID 56591901, compound

HRID 1616079Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[C:15]2[O:22][CH:21]=[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:16]=2[N:17]=[CH:18][N:19]=1.Cl[C:30]1[N:35]=[CH:34][C:33]([Cl:36])=[CH:32][N:31]=1.C(N(CC)C(C)C)(C)C.O>CN(C)C=O>[Cl:36][C:33]1[CH:32]=[N:31][C:30]([N:26]2[CH2:27][CH2:28][CH:23]([C:20]3[C:16]4[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:4]5[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:8][C:3]=5[F:2])[C:15]=4[O:22][CH:21]=3)[CH2:24][CH2:25]2)=[N:35][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-[2-fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (9.8 mg, 0.023 mmol), 2,5-dichloropyrimidine (5.1 mg, 0.035 mmol) and N,N-diisopropylethylamine (9.0 mg, 0.069 mmol) were dissolved in N,N-dimethylformamide (0.5 mL) and stirred at 80° C. for 2.5 hours. Water was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=25:1) to give the titled compound (2.2 mg, 19%) as a yellow solid.

Workup

customthe reaction liquid
extractionwas extracted with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure
customthe obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record: ord-e9d1d0d414d040e385e80a9e4020b8cb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765771B2

Reaction notes

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