Water → HCID 15147491, compound

HRID 255709Notes

Reaction equation

HRID 255709 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[C:9]=1[C:26](OCC)=O.O>O1CCCC1>[CH3:26][C:9]1[C:10]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[N:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:13][C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 15147484HCID 15147484, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15147491HCID 15147491, compoundYield 1.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (0.24 g) in dry tetrahydrofuran (40 ml) was dropwise added a solution of ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (2.0 g) in the same solvent (20 ml) under cooling at 7°-9° C. After the addition was completed, the mixture was stirred for 2 hours at room temperature. The excess lithium aluminum hydride was decomposed by a careful addition of water and the dried solution was concentrated in vacuo to an oil. The oil was column chromatographed on silica gel eluting with chloroform and the fractions containing a produce were collected and concentrated in vacuo. The residual crystals were recrystallized from n-hexane to give 5,6-dimethyl-2-phenyl-4-(4-pyridyl)pyrimidine (0.03 g), mp 152°-153° C.

Workup

  1. temperatureunder cooling at 7°-9° C
  2. additionAfter the addition
  3. concentrationthe dried solution was concentrated in vacuo to an oil
  4. customchromatographed on silica gel eluting with chloroform
  5. additionthe fractions containing a produce
  6. customwere collected
  7. concentrationconcentrated in vacuo
  8. customThe residual crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-b48a51b967d24395bfcf0ad9370c7439
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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