Cesium carbonate → N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine

HRID 449901Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[N:14]=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.C([O-])([O-])=O.[Cs+].[Cs+]>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].O1CCOCC1>[CH3:20][C:15]1[N:14]=[C:13]([NH:12][C:4]2[CH:3]=[C:2]([NH2:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=2)[CH:18]=[C:17]([CH3:19])[N:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a 200 ml flask was added 4-amino-2-chloro-5-nitropyridine (1.00 g, 5.76 mmol), 4-amino-2,6-dimethylpyrimidine (1.42 g, 11.5 mmol), Pd2(dba)3 (0.528 g, 0.576 mmol), XantPhos (0.400 g, 0.691 mmol), Cs2CO3 (4.13 g, 12.7 mmol) and dioxane (45 mL). The mixture was degassed with N2 for 2 min and then heated at 110° C. for 16 hrs. After cooling to room temperature the reaction was filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane) to give N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, yield: 23%). LCMS (ESI) m/z: 261.2 [M+H+].

Workup

customThe mixture was degassed with N2 for 2 min
temperatureAfter cooling to room temperature the reaction
filtrationwas filtered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-761d0ebbebfe4858934c252f17f95520
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

Loading…