Diethyl Ether → 5-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

HRID 255720Notes

Reaction equation

HRID 255720 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]=[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)[C:14]=1[C:34](OC)=[O:35]>O1CCCC1>[OH:35][CH2:34][C:14]1[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)=[N:16][C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:18][C:13]=1[CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15147475Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 103361765-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (12.24 g) in a mixture of dry tetrahydrofuran (180 ml) and diethyl ether (360 ml) was dropwise added a solution of methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylate in dry tetrahydrofuran (180 ml) under cooling at -50°~-40° C. The excess lithium aluminum hydride was decomposed by a careful addition to ice water. The separated organic layer was washed with 15% sulfuric acid (400 ml) and extracted with ethyl acetate (1 l). The organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively and concentrated in vacuo. The residue was recrystallized from diethyl ether to give 5-hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)-pyrimidine (30 g).

Workup

  1. temperatureunder cooling at -50°~-40° C
  2. washThe separated organic layer was washed with 15% sulfuric acid (400 ml)
  3. extractionextracted with ethyl acetate (1 l)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-2121b7a7b574441eac5fc9c4b604abcc
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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