Sodium Methoxide → 4-Amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

HRID 356647Notes

Reaction equation

HRID 356647 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[C:9](Cl)[N:8]=[C:7]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[N:6]=1>CO>[NH2:4][C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[C:9]([O:2][CH3:1])[N:8]=[C:7]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 189389064-Amino-6-chloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine

Product 1

HCID 229997224-Amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.55 g of sodium methylate were added at room temperature to a solution of 4-amino-6-chloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine in 200 ml of methanol and the solution was subsequently heated at reflux for 32 hours. The methanol was removed on a rotary evaporator, the residue was taken up in methylene chloride and washed with 1N hydrochloric acid. The organic phase was dried over magnesium sulphate, the solvent was finally removed in a water-jet vacuum. The crude product was chromatographed on silica gel with methylene chloride/ methanol (10/1) as the eluent. 4-Amino-6-methoxy-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine was obtained as a lemon-yellow powder MS: 325 (M).

Workup

  1. temperaturethe solution was subsequently heated
  2. temperatureat reflux for 32 hours
  3. customThe methanol was removed on a rotary evaporator
  4. washwashed with 1N hydrochloric acid
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customthe solvent was finally removed in a water-jet vacuum
  7. customThe crude product was chromatographed on silica gel with methylene chloride/ methanol (10/1) as the eluent

Sources & evidence

ORD record
ord-728c2f045cb849f2b1475878661e0416
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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