Methylamine → 4-(2-Methylamino-pyrimidin-4-yloxy)-benzene-1,2-diamine

HRID 491646Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:20][NH2:21]>C1COCC1>[CH3:20][NH:21][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=2)[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(2-methanesulfonyl-pyrimidin-4-yloxy)-benzene-1,2-diamine (Step B, 400 mg, 1.4 mmol, 1.0 eq) in anhydrous THF (4 mL) was added 1 mL of 2 M CH3NH2 in THF (2 mmol, 1.4 eq). The solution was heated to 80° C. for 1 h. The THF was removed under reduced pressure. The crude was purified by column chromatography (0-10% MeOH/CH2Cl2 with 1% NH4OH) to yield 4-(2-methylamino-pyrimidin-4-yloxy)-benzene-1,2-diamine.

Workup

customThe THF was removed under reduced pressure
customThe crude was purified by column chromatography (0-10% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record: ord-e81dd832725f48158bdf355ccb60d16f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531553B2

Reaction notes

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