Sodium Carbonate → HCID 66611911, compound

HRID 1812038Notes

Reaction equation

HRID 1812038 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:13]1[CH:14]=[C:15]([C:28]2[N:33]=[C:32]([CH3:34])[N:31]=[C:30]([N:35]([CH2:45][C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=3)[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[N:29]=2)[C:16]([NH:19][C:20]2[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)=[N:17][CH:18]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:44][O:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][N:35]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[C:30]2[N:31]=[C:32]([CH3:34])[N:33]=[C:28]([C:15]3[CH:14]=[C:13]([C:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH:18]=[N:17][C:16]=3[NH:19][C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[N:29]=2)=[CH:38][CH:39]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66611911HCID 66611911, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-methoxypyridin-3-ylboronic acid (0.039 g, 0.256 mmol), 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.1244 g, 0.213 mmol), Pd2dba3 (7.80 mg, 8.52 μmol), and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (8.12 mg, 0.017 mmol) was purged with argon. The mixture were treated with dioxane (2.0 mL) and sodium carbonate (0.27 mL, 0.53 mmol) and heated in a Biotage Initiator microwave at 140° C. for 30 min. The cooled reaction mixture was treated with 1 N NaOH and extracted with EtOAc (30 mL), washed with brine, dried over MgSO4, filtered and concentrated. The crude product was used directly in the next reaction. m/z (ESI, +ve ion) 657.0 (M+H)+.

Workup

  1. customwas purged with argon
  2. customThe cooled reaction mixture
  3. extractionextracted with EtOAc (30 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was used directly in the next reaction

Sources & evidence

ORD record
ord-a3a3f4c7c9964bfaa44643af4f2f0c88
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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