1,2-Dimethoxyethane → HCID 16124464, compound

HRID 1666266Notes

Reaction equation

Br[C:2]1[C:15](=[O:16])[N:14]([CH:17]([CH3:19])[CH3:18])[C:5]2[N:6]=[C:7]([NH:11][CH2:12][CH3:13])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.C(N(CC)CC)C.COCCOC>O>[CH2:12]([NH:11][C:7]1[N:8]=[C:9]([CH3:10])[C:4]2[CH:3]=[C:2]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)[C:15](=[O:16])[N:14]([CH:17]([CH3:19])[CH3:18])[C:5]=2[N:6]=1)[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

Pd(dppf) dichloromethane adduct (0.077 g, 0.095 mmol) was added to a suspension of 6-bromo-2-(ethylamino)-4-methyl-8-(1-methylethyl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.154 g, 0.474 mmol), 2-thiophene boronic acid (0.079 g, 0.616 mmol), and triethylamine (165 μL, 1.19 mmol) in 10:1 DME:water (1.5 mL). The reaction was heated to 100° C. After 5 h, the reaction was cooled to room temperature, filtered though a Celite plug and concentrated in vacuo. The residue was purified on SiO2 (3:2 hexanes:ethyl acetate) to give 2-(ethylamino)-4-methyl-8-(1-methylethyl)-6-(2-thienyl)pyrido[2,3-d]pyrimidin-7(8H)-one (28 mg, 18% yield) as a light yellow solid: 1H NMR (400 MHz, CDCl3): δ 8.06 (s, 1H), 7.60 (dd, J=4.0, 1.2 Hz, 1H), 7.38 (dd, J=5.2, 0.8 Hz, 1H), 7.10 (dd, J=4.8, 3.2 Hz, 1H), 5.93 (bsept, 1H), 5.13 (bs, 1H), 3.54 (pent, J=7.2 Hz, 2H), 2.61 (s, 3H), 1.66 (d, J=6.8 Hz, 6H), 1.28 (t, J=7.6 Hz, 3H); MS (EI) for C17H20N4OS: 329.0

Workup

temperaturethe reaction was cooled to room temperature
filtrationfiltered though a Celite plug
concentrationconcentrated in vacuo
customThe residue was purified on SiO2 (3:2 hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-aa338ecf8aab4e5cb0531aa0c19dca29
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044062B2

Reaction notes

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