Sodium Carbonate → HCID 59592879, compound

HRID 2098710Notes

Reaction equation

HRID 2098710 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH:33]=[N:34][NH:35]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[NH:35]1[C:36]2[C:32](=[C:31]([C:2]3[N:3]=[C:4]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:5]4[O:10][C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)=[CH:8][C:6]=4[N:7]=3)[CH:39]=[CH:38][CH:37]=2)[CH:33]=[N:34]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59593145HCID 59593145, compound

Product 1

HCID 59592879HCID 59592879, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-4-morpholino-6-phenylfuro[3,2-d]pyrimidine 44 (50 mg, 1.0 eq) was dissolved in toluene/ethanol/water (4:2:1, 2.8 ml) and treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (97 mg, 2.5 eq), PdCl2(PPh3)2 (13.3 mg, 0.12 eq) and sodium carbonate (59 mg, 3.5 eq). The vial was sealed and heated with stirring in the microwave to 150° C. for 25 minutes. The crude reaction mixture was concentrated and purified by reverse phase HPLC to afford 201 MS (Q1) 398 (M)+.

Workup

  1. customThe vial was sealed
  2. temperatureheated
  3. customThe crude reaction mixture
  4. concentrationwas concentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-64be78492d48487ba964440961c46c18
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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