Sodium Carbonate → HCID 59380007, compound

HRID 2353711Notes

Reaction equation

HRID 2353711 reaction equation
[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]1[N:29]=[C:28]([CH2:30][S:31]([CH:34]2[CH2:36][CH2:35]2)(=[O:33])=[O:32])[CH:27]=[C:26]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]2[CH3:43])[N:25]=1>CN(C=O)C.COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:24]3[N:29]=[C:28]([CH2:30][S:31]([CH:34]4[CH2:36][CH2:35]4)(=[O:32])=[O:33])[CH:27]=[C:26]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]4[CH3:43])[N:25]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380174HCID 59380174, compound

Product 1

HCID 59380007HCID 59380007, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
100 °C

Procedure

[4-(3-Cyclopropylureido)phenyl]boronic acid, pinacol ester (80 mg, 0.26 mmol), sodium carbonate (1.055 mL, 2.11 mmol), dichlorobis(triphenylphosphine)palladium(II) (14.8 mg, 0.02 mmol) and 2-chloro-4-(cyclopropylsulfonylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (70 mg, 0.21 mmol) were suspended in 18% DMF in DME:Ethanol:Water 7:2:3 mixture (4 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 10 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol. The crude product was further purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material as a colourless gum (33.0 mg).

Workup

  1. customsealed into a microwave tube
  2. temperaturecooled to RT
  3. customThe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customThe crude product was further purified by preparative HPLC

Sources & evidence

ORD record
ord-492abfbdd61340f59a283f34016485e9
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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