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

HRID 1396822
Notes
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Reaction equation

HRID 1396822 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1606792-O-MethylcytosineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59823198N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine

Product 1

HCID 68650127N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamineYield 48%

Reagents, catalysts & solvents 1

HCID 167845
palladium(II) acetate
Catalyst

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

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

Sources & evidence

ORD record
ord-fb27853d38284dce9cd5424dd53c1920
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901143B2

Reaction notes

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