1,1-Dimethoxyethyl(dimethyl)amine → HCID 69070361, compound

HRID 216147Notes

Reaction equation

HRID 216147 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:4]=1.CO[C:31](OC)([N:33]([CH3:35])[CH3:34])[CH3:32]>O>[CH3:34][N:33]([CH3:35])[C:31]([CH3:32])=[CH:16][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:7]2[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[N:4]=[C:3]([O:2][CH3:1])[N:8]=2)[CH:10]=1)=[O:17]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 53321839HCID 53321839, compound

Product 1

HCID 69070361HCID 69070361, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-ethanone [125 mg, 0.33 mmol, Example 35(h)] and dimethylacetamide dimethylacetal (2 mL) in a round bottom flask is heated to 90° C. for 4 hours. The reaction mixture is treated with water (20 mL) and extracted three times with EtOAc (20 mL). The combined organics are dried over magnesium sulfate, filtered and concentrated by rotary evaporator to provide 3-dimethylamino-1-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-but-2-en-1-one [Intermediate (47)] in quantitative yield.

Workup

  1. extractionextracted three times with EtOAc (20 mL)
  2. dry with materialThe combined organics are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-fee45dc8007948238cb90351081c1a85
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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