Potassium sodium tartarate → HCID 46831271, compound

HRID 2368779Notes

Reaction equation

HRID 2368779 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](OC)=[O:18])=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[N:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[N:29][CH:30]=[N:31][CH:32]=2)=[N:23][C:22]=1[NH:33][C:34]1[CH:35]=[C:36]([NH2:41])[CH:37]=[CH:38][C:39]=1[CH3:40].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[N:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[N:29][CH:30]=[N:31][CH:32]=2)=[N:23][C:22]=1[NH:33][C:34]1[CH:35]=[C:36]([NH:41][C:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[CH:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[CH2:9][CH2:10]3)=[O:18])[CH:37]=[CH:38][C:39]=1[CH3:40]

Participants

6

Reactant 4

HCID 9855836Potassium sodium tartarateHCID 16682925Trimethylaluminum2×HCID 231458394-Methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]anilineHCID 58579023HCID 58579023, compound

Product 1

HCID 46831271HCID 46831271, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxylate (823 g, 3 mmol) and N(3)-4,5′-bipyrimidin-2-yl-4-methyl benzene-1,3-diamine (973 g, 3.5 mmol) were suspended in 15 mL of toluene, and then a 2 M trimethylaluminium solution (3 mL, 6 mmol) was added. The mixture was stirred overnight at 50° C. and another 2 M trimethylaluminium solution (2 mL, 4 mmol) was added. The solution was stirred overnight at 60° C. and then cooled in an ice bath. Saturated aqueous solution of potassium sodium tartrate was added with stirring. The solution obtained was extracted with methylene chloride (3×100 mL). The pooled extracts were washed with sodium bicarbonate (100 mL) and with brine (2×100 mL), dried over magnesium sulfate, concentrated, and purified by silica gel column chromatography using 50% ethyl acetate/methylene chloride/5-10% triethylamine as eluent to obtain 702 mg of the title compound (45% yield). MS (M+1)=527.27. 1HNMR (DMSO-d6, ppm): δ 10.10 (s, 1H); 9.46 (s, 2H); 9.28 (s, 1H); 9.08 (s, 1H); 8.50 (d, J=5.7 Hz, 1H); 8.04 (s, 1H); 7.74 (s, 1H); 7.70 (d, J=9.0 Hz, 1H); 7.46 (d, J=5.7 Hz, 1H); 7.42 (d, J=9.0 Hz, 1H); 7.32 (d, J=9.0 Hz, 1H); 7.15 (d, J=9.0 Hz, 1H); 4.25 (t, J=5.7 Hz, 1H); 2.2-2.9 (m, 10H); 2.15 (s, 3H); 2.07 (s, 3H); 2.0 (m, 2H).

Workup

  1. stirringThe solution was stirred overnight at 60° C.
  2. temperaturecooled in an ice bath
  3. stirringwith stirring
  4. customThe solution obtained
  5. extractionwas extracted with methylene chloride (3×100 mL)
  6. washThe pooled extracts were washed with sodium bicarbonate (100 mL) and with brine (2×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-fbd11d12237848738ed3ba84cddf7724
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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