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

HRID 2353638
Notes
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Reaction equation

HRID 2353638 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27346154-Aminophenylboronic acidHCID 593799432-Methylsulfanyl-4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine

Product 1

HCID 593800394-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine-2-yl]aniline

Reagents, catalysts & solvents 3

HCID 11194830Cuprous 2-thiophenecarboxylateCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

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

  1. customThe system was degassed with N2
  2. customsealed
  3. temperatureUpon cooling the reaction
  4. additionwas poured into water
  5. filtrationthe resulting precipitate was collected by filtration
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes