Sodium Carbonate → HCID 59379868, compound

HRID 2353712Notes

Reaction equation

HRID 2353712 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.Cl[C:18]1[N:23]=[C:22]([C:24]([S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]2[CH3:39])[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O.CCO>CN(C=O)C.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:18]3[N:23]=[C:22]([C:24]([S:27]([CH:30]4[CH2:31][CH2:32]4)(=[O:28])=[O:29])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380019HCID 59380019, compoundHCID 86587095Dimethoxyethane ethanol water

Product 1

HCID 59379868HCID 59379868, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

[4-(3-Cyclopropylureido)phenyl]boronic acid, pinacol ester (199 mg, 0.66 mmol), 2-chloro-4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (190 mg, 0.53 mmol), sodium carbonate (1.320 mL, 2.64 mmol) and dichlorobis(triphenylphosphine)palladium(II) (37.1 mg, 0.05 mmol) were suspended in 18% DMF in a DME:Water:EtOH 7:3:2 solution (4 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 20 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 and pure fractions were evaporated to dryness. 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 white solid (85 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. customwere evaporated to dryness
  6. customThe crude product was further purified by preparative HPLC

Sources & evidence

ORD record
ord-ab112ebc83604480a1cbd366c0e17bc8
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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