Cesium carbonate → 6-(4-Methoxybenzyl)-9-(piperazin-1-ylmethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5 (6H)-one

HRID 926119Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[CH:17][C:12]=3[C:11]3=[N:32][CH:33]=[N:34][N:10]3[C:9]2=[O:35])=[CH:5][CH:4]=1.BrC1C=NC2N(CC3C=CC(OC)=CC=3)C(=O)N3N=CN=C3C=2C=1.C(OC(N1CCN(C[B-](F)(F)F)CC1)=O)(C)(C)C.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:17][C:12]=3[C:11]3=[N:32][CH:33]=[N:34][N:10]3[C:9]2=[O:35])=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-((6-(4-methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-9-yl)methyl)piperazine-1-carboxylate. 9-Bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 1, 562.00 mg; 1.46 mmol), potassium ((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)trifluoroborate (568.00 mg; 1.86 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (60.00 mg; 0.13 mmol;), Pd(OAc)2 (30.00 mg; 0.13 mmol), Cs2CO3 (1.76 g; 5.40 mmol), and degassed dioxane-water (9:1; 10 mL) were combined in that order and heated at 80° C. for 4 days. The mixture concentrated under reduced pressure. Purification (FCC, SiO2, 20-100% EtOAc/hexanes) afforded the title compound (216 mg, 29%).

Workup

concentrationThe mixture concentrated under reduced pressure
customPurification (FCC, SiO2, 20-100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ef88f57f16f348e2896c15c93dcd5e3b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284335B2

Reaction notes

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