1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → [5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

HRID 1971609Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH2:18])[N:17]=[C:13]3[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Br[C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[O:23][CH2:24][CH2:25][N:26]1[CH:30]=[CH:29]N=[CH:27]1.[CH3:34]C1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>CC(N(C)C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:33]4[CH:32]=[CH:31][C:22]([O:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:34][CH2:27]5)=[CH:21][CH:20]=4)[N:17]=[C:13]3[CH:12]=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In a microwave vial, 5-(4-methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-ylamine (0.05 g, 0.207 mmol), 1-[2-(3-bromo-phenoxy)-ethyl]-1H-imidazole (0.073 g, 0.27 mmol), bis(dibenzylideneacetone)palladium (0.01 g, 0.01 mmol), xantphos (0.012 g, 0.02 mmol) and sodium tert butoxide (0.04 g, 0.416 mmol) were added successively. 1,4-Dioxane (1.2 mL) and dimethylacetamide (4 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The mixture was filtered and purified by preparatory LCMS. LCMS method: 1, RT: 3.27 min; MI: 431 [M+1].

Workup

customthe vial was sealed
filtrationThe mixture was filtered
custompurified by preparatory LCMS

Sources & evidence

ORD record: ord-3bf3bc389d794ffba6602650b5ae4120
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431596B2

Reaction notes

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