4-Aminotetrahydropyran → HCID 25016748, compound

HRID 1991021Notes

Reaction equation

[CH:1]1([N:6]2[C:11]3[N:12]=[C:13](S(C)=O)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:34])[C:7]2=[O:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:36][CH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CC(O)C>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:36][CH:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:34])[C:7]2=[O:35])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 8-cyclopentyl-6-{5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl}-2-methane-sulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.04 g, 0.08 mmol) and 4-aminotetrahydropyran (0.041 g, 0.40 mmol) in 2-propanol (2 mL) was heated in a microwave reactor at 120° C. for 1 hour. The reaction mixture was cooled and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 50-70% ethyl acetate in hexanes to give 8-cyclopentyl-6-{5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl}-2-(tetrahydro-pyran-4-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (Yield: 16.0 mg, 38%). HRMS (ES+) m/z Calcd for C30H36N6O3. +H [(M+H)+]: 529.2922. Found: 529.2917.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with 50-70% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-790bfd151e1c44a6bc40b8cf843b8c93
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645764B2

Reaction notes

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