2-Bromoethyl methyl ether → HCID 22636781, compound

HRID 2416339Notes

Reaction equation

HRID 2416339 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)=[C:12]([O:26][CH2:27][CH3:28])[CH:11]=2)=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH3:35][O:36][CH2:37][CH2:38]Br>CN(C)C=O>[CH2:27]([O:26][C:12]1[CH:11]=[C:10]([CH2:9][C:5]2[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:38][CH2:37][O:36][CH3:35])[CH:20]=1)[CH3:28]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 22636959HCID 22636959, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22636781HCID 22636781, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4′-(2,4-Diamino-pyrimidin-5-ylmethyl)-2′,6′-diethoxy-biphenyl-3-ol (200 mg; 0.526 mmol) is suspended in dimethylformamide (5 ml; dried over a molecular sieve), and potassium tert-butylate (83 mg; 0.736 mmol) is added at room temperature. 2-Bromoethyl methyl ether (0.059 ml; 0.63 mmol) in dimethylformamide (5 ml; dried over a molecular sieve) is added in the course of 35 minutes to the solution formed. After stirring at room temperature for 12 hours, the reaction mixture is concentrated and the residue is stirred successively with water (twice) and diethyl ether, filtered off with suction and dried under a high vacuum.

Workup

  1. additionis added at room temperature
  2. customdried over a molecular sieve)
  3. additionis added in the course of 35 minutes to the solution
  4. customformed
  5. concentrationthe reaction mixture is concentrated
  6. stirringthe residue is stirred successively with water (twice) and diethyl ether
  7. filtrationfiltered off with suction
  8. customdried under a high vacuum

Sources & evidence

ORD record
ord-4ff088f4dded4a949bdd91d88ab9de5b
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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