Hydrochloric Acid → 24NH2PYRIMIDN,5(35ETO-4-ACETYL)BENZYL

HRID 1579316Notes

Reaction equation

HRID 1579316 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](=[O:25])[CH2:20]S(C)(=O)=O)=[C:12]([O:26][CH2:27][CH3:28])[CH:11]=2)=[CH:4][N:3]=1.[Al].Cl>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:26][CH2:27][CH3:28])[C:13]([C:19](=[O:25])[CH3:20])=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5359268Aluminum2×HCID 232770301-[4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-diethoxyphenyl]-2-methylsulfonylethanone

Product 1

HCID 2327635824NH2PYRIMIDN,5(35ETO-4-ACETYL)BENZYL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5.8 g. of 4'-[(2,4-diamino-5-pyrimidinyl)-methyl] -2',6'-diethoxy-2-(methylsulfonyl)acetophenone in 50 ml. of 20% aqueous tetrahydrofuran is reduced with 1 g. of amalgamated aluminum at 65° over a period of 4 hours. (The aluminum chips are immersed in a 2% hydrochloric acid solution for 2 minutes, rinsed with methanol, and thereafter used in the reduction.) The reaction mixture is filtered warm, the filtrate is concentrated and adjusted to a pH of 9 with 5% sodium hydroxide. The resulting solution is then shaken with five 50 ml. portions of ethyl acetate. The resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1) yields 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone, having a m.p. of 229°-231° recrystallized from methanol.

Workup

  1. additionA suspension of 5.8 g
  2. washrinsed with methanol
  3. filtration) The reaction mixture is filtered
  4. temperaturewarm
  5. concentrationthe filtrate is concentrated
  6. washThe resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1)

Sources & evidence

ORD record
ord-732863ce30e940678da669ce641395cf
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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