Ammonium Hydroxide → 5-[4-(2,6-Dimethyl-pyridin-4-yl)-3,5-diethoxy-benzyl]-pyrimidine-2,4-diamine

HRID 2416304Notes

Reaction equation

HRID 2416304 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].[C:23]([C:27]1C=[C:31](C)[CH:30]=[C:29](C(C)(C)C)[C:28]=1O)(C)(C)[CH3:24].[NH4+:39].[OH-]>CN(C)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>[CH3:24][C:23]1[CH:27]=[C:28]([C:18]2[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([CH2:7][C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)=[CH:16][C:17]=2[O:20][CH2:21][CH3:22])[CH:29]=[C:30]([CH3:31])[N:39]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 226369195-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine

Product 1

HCID 226367855-[4-(2,6-Dimethyl-pyridin-4-yl)-3,5-diethoxy-benzyl]-pyrimidine-2,4-diamineYield 6.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

5-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (414 mg; 1 mmol), 2,6-dimethyl-4-trimethyltin-pyridine (404 mg; 1.5 mmol), bis(triphenyl-phosphine)palladium dichloride (20 mg) and a few crystals of 2,6-di-tert-butyl-4-methylphenol are dissolved in dimethylformamide (5 ml) and the solution is stirred for 24 hours at 140° C. while gassing with argon. The reaction mixture is concentrated, a little water is added to the residue obtained, the pH is adjusted to 8 by addition of NH4OH conc. and the entire mixture is filtered with suction. The mother liquor is concentrated and the residue is chromatographed over silica gel (30 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05). 26 mg (6.6%) 5-[4-(2,6-dimethyl-pyridin-4-yl)-3,5-diethoxy-benzyl]-pyrimidine-2,4-diamine are obtained as a yellow powder.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additiona little water is added to the residue
  3. customobtained
  4. filtrationthe entire mixture is filtered with suction
  5. concentrationThe mother liquor is concentrated
  6. customthe residue is chromatographed over silica gel (30 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05)

Sources & evidence

ORD record
ord-faa95fea33654851915a4eaca879b586
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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