Triethylamine → 6-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine

HRID 1049924Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:11]=[C:10](C3C=C(C=C(F)C=3)C(NCC3CCN(C)CC3)=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1.C(N(CC)CC)C.CC(N(C)C)=O>ClCCl>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:10]2[CH:9]=[CH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[N:11]=2)[CH2:37]1

Participants

Conditions

Temperature: 100 °C

Procedure

To an 8 mL screw-cap vial was added 6-chloropyrido[3,2-d]pyrimidin-4-amine 10 (1 equiv., 0.68 mmol, 123 mg), 3-(1H-imidazol-2-yl)piperidine hydrochloride (1 equiv., 0.68 mmol, 128 mg), triethylamine (3 equiv., 2.05 mmol, 0.287 mL) and DMA (2 mL). The reaction was capped and shaken at 100° C. overnight. The reaction was then cooled to room temperature, diluted with dichloromethane, and washed with water. The organic was then concentrated, then purified by reverse phase HPLC, yielding 16 mg of product. 1H NMR (400 MHz, DMSO) δ 8.20-8.14 (m, 3H), 7.82-7.77 (m, 1H), 7.54-7.49 (d, J=9.4 Hz, 1H), 7.38-7.28 (d, J=8.1 Hz, 2H), 6.96-6.94 (s, 2H), 4.79-4.71 (d, J=12.7 Hz, 1H), 4.53-4.46 (d, J=17.4 Hz, 1H), 3.17-3.07 (m, 1H), 3.07-2.96 (m, 1H), 2.96-2.84 (m, 1H), 2.18-2.08 (m, 1H), 1.91-1.77 (m, 2H), 1.66-1.51 (m, 1H). LCMS M/Z (M+H)=296.

Workup

customTo an 8 mL screw-cap vial
customThe reaction was capped
temperatureThe reaction was then cooled to room temperature
washwashed with water
concentrationThe organic was then concentrated
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-eb9212c002f64c099a0e8fde9506ae6f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382241B2

Reaction notes

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