4-Aminophenylboronic acid → 4-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine-2-yl]aniline

HRID 2353638Notes

Reaction equation

CS[C:3]1[N:8]=[C:7]([CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:6]=[C:5]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:4]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>S1C=CC=C1C([O-])=O.[Cu+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:13][S:10]([CH2:9][C:7]1[CH:6]=[C:5]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:4]=[C:3]([C:24]2[CH:25]=[CH:26][C:21]([NH2:20])=[CH:22][CH:23]=2)[N:8]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 130 °C

Procedure

2-Methylsulfanyl-4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine (1.00 g, 3.3 mmol), 4-aminophenylboronic acid (904 mg, 6.60 mmol), Copper(I)thiophene-2-carboxylate (1.64 g, 8.58 mmol), Pd(PPh3)4 (153 mg, 0.04 equiv., 0.13 mmol) were added to a microwave vessel and 1,4-Dioxane (20 mL) added. The system was degassed with N2, sealed and heated in a microwave reactor at 130° C. for 1 hour. Upon cooling the reaction was poured into water and the resulting precipitate was collected by filtration and dried under vacuum to afford the title compound as an off-white solid. (988 mg)

Workup

customThe system was degassed with N2
customsealed
temperatureUpon cooling the reaction
additionwas poured into water
filtrationthe resulting precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-a90a78aa637941a4bd1fa8f83e4f7ec0
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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