24NH2PYRIMIDN,5(35MEO-4COCH2SO2ME)BENZYL → Acetophenone, 4-(2,4-diamino-5-pyrimidinylmethyl)-2,6-dimethoxy-

HRID 1579317Notes

Reaction equation

HRID 1579317 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][CH3:17])[C:13]([C:18](=[O:24])[CH2:19]S(C)(=O)=O)=[C:12]([O:25][CH3:26])[CH:11]=2)=[CH:4][N:3]=1.[Al]>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:25][CH3:26])[C:13]([C:18](=[O:24])[CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 304355224NH2PYRIMIDN,5(35MEO-4COCH2SO2ME)BENZYLHCID 5359268Aluminum

Product 1

HCID 41524Acetophenone, 4-(2,4-diamino-5-pyrimidinylmethyl)-2,6-dimethoxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.0 g. of 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-dimethoxy-2-(methylsulfonyl)-acetophenone in 80 ml. of 20% aqueous tetrahydrofuran is reduced with 1 g. of amalgamated aluminum at 40° over a period of 1 hour. The reaction mixture is filtered and the filtrate is concentrated to 1/3 its original volume and is adjusted to a pH of 9 with 4N sodium hydroxide solution. The precipiated product is taken up in ethyl acetate. The ethyl acetate extracts are dried over magnesium sulfate and evaporated. The residue is recrystallized from methanol and there is obtained 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-dimethoxy-acetophenone, having a m.p. of 282°-285° (with decomposition).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated to 1/3 its original volume
  3. dry with materialThe ethyl acetate extracts are dried over magnesium sulfate
  4. customevaporated
  5. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-fc1c1e82521042fda08c5e158512c9b0
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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