Methylamine → HCID 58405769, compound

HRID 44829Notes

Reaction equation

[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][NH2:28]>CCN(CC)CC>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:28][CH3:27])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 200 mg, 0.56 mmol) in methylamine (5 mL of 2M in CH3OH), 1 mL of Et3N was added. The mixture was stirred at 110° C. in a sealed tube for 18 h, and then concentrated under reduced pressure, quenched with water and extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure, and chromatographed (CH2Cl2:CH3OH=10:1) to give the title compound as a white solid (150 mg, 70% yield). 1H NMR (CDCl3) δ: 9.76 (broad, 1H), 8.08 (s, 1H) 7.85 (d, 1H), 7.74 (s, 1H), 7.58 (d, 1H), 4.40 (m, 2H), 3.43 (s, 3H), 3.1 (s, 3H), 2.2-1.7 (m, 10H) and 0.89 ppm (t, 3H); LCMS: 367.2 m/z (M+H)+; ret. Time: 1.44 min (Analytical Method E).

Workup

concentrationconcentrated under reduced pressure
customquenched with water
extractionextracted with EtOAc
dry with materialThe combined organic phase was dried with Na2SO4
concentrationconcentrated under reduced pressure
customchromatographed (CH2Cl2:CH3OH=10:1)

Sources & evidence

ORD record: ord-f2c472cc80c14b8fa1ff403c98af04ae
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

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