Sodium Carbonate → HCID 22637054, compound

HRID 2416309Notes

Reaction equation

HRID 2416309 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](Br)=[C:12]([O:20][CH2:21][CH3:22])[CH:11]=2)=[CH:4][N:3]=1.[C:23](=[O:26])([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[CH2:17]([O:16][C:14]1[CH:15]=[C:10]([CH2:9][C:5]2[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:11]=[C:12]([O:20][CH2:21][CH3:22])[C:13]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:26][CH3:23])[CH:11]=1)[CH3:18]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 22636840HCID 22636840, compound

Product 1

HCID 22637054HCID 22637054, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Tetrakis-triphenylphosphine-palladium (57 mg; 0.050 mmol) is suspended in dimethoxyethane (1 ml), while gassing with argon, and 2,4-diamino-5-(4-bromo-3,5-diethoxybenzyl)pyrimidine (367 mg; 1 mmol) in dimethoxyethane (6 ml) is added. After stirring for a quarter of an hour at room temperature, 3-methory-phenylboron acid (228 mg; 1.5 mmol) in ethanol (1.5 ml) is added, the mixture is stirred for a further 5 minutes at room temperature, an aqueous 2 M sodium carbonate solution (4.2 ml; 8.5 mmol) is added and the mixture is then boiled under reflux (bath temperature 85° C.) for 2.5 hours. The reaction mixture is concentrated and the residue is stirred with water and a little methanol and filtered off with suction. The filter cake is stirred with water, filtered off with suction and dried under a high vacuum.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for a further 5 minutes at room temperature
  3. temperatureunder reflux (bath temperature 85° C.) for 2.5 hours
  4. concentrationThe reaction mixture is concentrated
  5. stirringthe residue is stirred with water
  6. filtrationa little methanol and filtered off with suction
  7. stirringThe filter cake is stirred with water
  8. filtrationfiltered off with suction
  9. customdried under a high vacuum

Sources & evidence

ORD record
ord-f094052afd3b406683e64300fd07fab0
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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