Dimethylethylamine → (2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl){2-methyl-6-[(2,4,6-trimethylphenyl)amino]pyrimidin-4-yl}amine

HRID 1634571Notes

Reaction equation

HRID 1634571 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[C:21]([NH:23][C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])[N:20]=[C:19]([CH3:33])[N:18]=2)=O)=[CH:6][C:5]=1[O:34][CH3:35])[CH3:2].[AlH3].N(CC)(C)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[C:21]([NH:23][C:24]3[C:25]([CH3:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=3[CH3:30])[N:20]=[C:19]([CH3:33])[N:18]=2)=[CH:6][C:5]=1[O:34][CH3:35])[CH3:2]

Participants

5

Reactant 3

HCID 11723DimethylethylamineHCID 14488Aluminum hydrideHCID 220341212-(4-Ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide

Product 1

HCID 22034147(2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl){2-methyl-6-[(2,4,6-trimethylphenyl)amino]pyrimidin-4-yl}amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Heat a solution of 2-(4-ethoxy-3methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide (0.324 g, 0.68 mmol) in THF (10 mL) with AlH3.NMe2Et (14 mL, 6.78 mmol) to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O (1.0 g) and stir at ambient temperature for 15 min. Filter the solution through Celite and wash with several portions of CH2Cl2. Concentrate the filtrate in vacuo to dryness and purify by preparative TLC (10% MeOH in CH2Cl2) to obtain the title compound.

Workup

  1. customquench with Na2CO3.10H2O (1.0 g)
  2. filtrationFilter the solution through Celite
  3. washwash with several portions of CH2Cl2
  4. concentrationConcentrate the filtrate in vacuo to dryness
  5. custompurify by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-fd5a80e2f1244bdcbec5447d096e7a84
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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