Sodium Carbonate → HCID 59198408, compound

HRID 1920832Notes

Reaction equation

HRID 1920832 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[N:18][CH:19]=2)[N:3]=1.[CH3:27][O:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:27][O:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=[C:4]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[N:18][CH:19]=3)[N:3]=2)[CH:32]=[N:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59198390HCID 59198390, compound

Product 1

HCID 59198408HCID 59198408, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of N-(5-(4-chloro-6-morpholinopyrimidin-2-yl)pyridine-2-yl)pivalamide (50 mg, 0.133 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (94 mg, 0.399 mmol) and Pd(dppf)Cl2-CH2Cl2 (16 mg, 0.020 mmol) in 2 mL of dimethoxyethane:2 M Na2CO3 (3:1) is heated under microwave irradiation for 15 minutes at 130° C. (normal absorption, fixed hold time). The reaction mixture is partitioned between EtOAc (50 mL) and H2O (10 mL); the organic layer is separated, washed with brine (7 mL), dried over Na2SO4, filtered and concentrated. The residue thus obtained is used in the next step without further purification.

Workup

  1. custom(normal absorption, fixed hold time)
  2. customThe reaction mixture is partitioned between EtOAc (50 mL) and H2O (10 mL)
  3. customthe organic layer is separated
  4. washwashed with brine (7 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customis used in the next step without further purification

Sources & evidence

ORD record
ord-8a26fe0bbbf8486099b13222c1b720b0
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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