Potassium Phosphate, Tribasic → 7-chloro-2-methyl-1-(3-methylbutyl)-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one

HRID 530130Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:19])[C@H:11]([CH3:18])[NH:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O>[Cl:8][C:6]1[N:5]=[CH:4][C:3]2[NH:9][C:10](=[O:19])[CH:11]([CH3:18])[N:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a stirred solution of N-(4,6-dichloropyridin-3-yl)-N2-(3-methylbutyl)alaninamide (350 mg, 1.15 mmol) in DMF (1.0 mL) was added tri-basic potassium phosphate (250 mg, 1.20 mmol). The reaction mixture was heated to 125° C. and stirred at the same temperature for 3 h. The reaction was then cooled to rt, diluted with water (5 mL) and the aqueous phase was extracted with ethyl acetate (25 mL×3). The combined organic phases were washed with water, dried over Na2SO4 and evaporated to give desired product (Yield: 33%), which was used for next step without any further purifications. 1HNMR (CDCl3, 300 MHz) δ 0.90-1.01 (m, 6H), 1.33 (d, 3H), 1.52-1.75 (m, 2H), 1.80 (s, 1H), 3.10-3.19 (m, 1H), 3.31-3.42 (m, 1H), 4.07 (q, 1H), 6.51 (s, 1H), 7.65 (s, 1H), 9.41 (br s, 1H).

Workup

temperatureThe reaction was then cooled to rt
extractionthe aqueous phase was extracted with ethyl acetate (25 mL×3)
washThe combined organic phases were washed with water
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-47de49c990d74351951366bdcf353e76
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351974B2

Reaction notes

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