Hydrochloric Acid → HCID 57833268, compound

HRID 729926Notes

Reaction equation

HRID 729926 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.Cl[C:27]1[CH:32]=[C:31]([O:33][C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:41]3[CH:46]=[C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:44]=[C:43]([NH2:53])[N:42]=3)=[CH:36][CH:35]=2)[CH:30]=[CH:29][N:28]=1.[Li+].C[Si]([N-:59][Si](C)(C)C)(C)C.Cl.[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]>[NH2:59][C:27]1[CH:32]=[C:31]([O:33][C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:41]3[CH:46]=[C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:44]=[C:43]([NH2:53])[N:42]=3)=[CH:36][CH:35]=2)[CH:30]=[CH:29][N:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 57833225HCID 57833225, compound

Product 1

HCID 57833268HCID 57833268, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
65 °C

Procedure

To a 8-mL vial was added Pd2(dba)3 (0.028 g, 0.03 mmol), 2-dicyclohexylphosphinobiphenyl (0.025 g, 0.070 mmol), and N4-{4-[(2-chloropyridin-4-yl)oxy]phenyl}&phenylpyrimidine-2,4-diamine (0.20 g, 0.51 mmol, Example 48). The vial was sealed, evacuated, and back filled with nitrogen. THF was then added via syringe, followed by addition of LiHMDS (1M in THF, 0.72 mL, 0.72 mmol). The mixture was heated at 65° C. overnight. The mixture was then cooled to rt, treated with 1N HCl, and stirred for 12 h at rt. The mixture was then neutralized using 1N NaOH and extracted with methylene chloride (10 mL×3). The organic extracts were combined, washed with brine, dried over magnesium sulfate, and purified by preparative HPLC to furnish 0.035 g of the desired product (18%). 1H NMR (CD3OD) δ 7.96 (d, 2H), 7.79 (m, 3H), 7.60 (m, 3H), 7.22 (m, 2H), 6.61 (d, 1H), 6.58 (s, 1H), 6.20 (s, 1H); MS ES 371 (M+H)+ calcd 371.

Workup

  1. customThe vial was sealed
  2. customevacuated
  3. additionback filled with nitrogen
  4. additionTHF was then added via syringe
  5. temperatureThe mixture was then cooled to rt
  6. extractionextracted with methylene chloride (10 mL×3)
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ba54c781c873427781cdf0b9d28426dc
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

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