1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (R)-N-(1-(4-Chlorophenyl)ethyl)-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

HRID 241873Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]2[C:12]3[CH2:20][NH:19][CH2:18][CH2:17][C:13]=3[N:14]=[CH:15][N:16]=2)[CH3:9])=[CH:4][CH:3]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1.CC1(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+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]2[C:12]3[CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=4)[CH2:18][CH2:17][C:13]=3[N:14]=[CH:15][N:16]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (R)-N-(1-(4-chlorophenyl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (80.0 mg, 0.277 mmol), 2-bromo-5-chloropyridine (69 mg, 0.36 mmol), dry toluene (5 mL), xantphos (10 mg, 0.02 mmol), sodium tert-butoxide (40 mg, 0.42 mmol), and tris(dibenzylideneacetone)dipalladium(0) (6.3 mg, 0.0069 mmol) under N2 was heated in an oil bath at 100° C. for 1.5 h. The mixture was absorbed on silica gel and purified by column (0-5% MeOH/CH2Cl2) to afford a light tan powder.

Workup

customThe mixture was absorbed on silica gel
custompurified by column (0-5% MeOH/CH2Cl2)
customto afford a light tan powder

Sources & evidence

ORD record: ord-e5c0af950a1f493bbeebfdc95b1e00fd
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653091B2

Reaction notes

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