2-O-Methylcytosine → N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine

HRID 1801717Notes

Reaction equation

CO[C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][N:4]=1.Cl[C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22]([CH3:27])=[CH:21]3)[CH:14]=[CH:13][N:12]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:49][C:31]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:31][O:49][C:11]1[N:16]=[C:15]([N:17]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22]([CH3:27])=[CH:21]3)[C:3]2[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][N:4]=2)[CH:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 2-methoxypyrimidin-4-amine (0.1 mmol) and N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1 mmol) in 3 ml dioxide, CsCO3 (0.2 mmol), Pd(OAc)2(10 mmol %) and Xantphos (10 mmol %) were added. The mixture was stirred under microwave irradiation at 200° C. for 40 mins. After cooling the solution was filtered and the filtrate was concentrated in vacuo, the residue was purified by column chromatography(C-18) to give N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine (yield 48%).

Workup

temperatureAfter cooling the solution
filtrationwas filtered
concentrationthe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography(C-18)

Sources & evidence

ORD record: ord-fd6d634c16754eb49734eac9c516653b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349859B2

Reaction notes

Loading…