Methanol → HCID 70245282, compound

HRID 651415Notes

Reaction equation

HRID 651415 reaction equation
[OH:1][C@H:2]1[CH2:7][O:6][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)OC1.ClC1[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[N:18]=[CH:17][N:16]=1.O1CCC[CH2:25]1.[H-].[Na+].[CH3:31][OH:32]>>[Cl:21][C:20]1[C:31]([O:32][C@H:2]2[CH2:7][O:6][C@@H:5]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:25][O:1]2)=[N:16][CH:17]=[N:18][C:19]=1[CH2:22][CH3:23]

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 178521647HCID 178521647, compound

Product 1

HCID 70245282HCID 70245282, compound

Procedure

1.8 g (10 mmol) of cis-5-hydroxy-2-phenyl-1,3-dioxane (E. Juaristi, S. Antunez, Tetrahedron 48, 5941 (1992), incorporated herein by reference) and 1.8 g of 4,5-dichloro-6-ethyl-pyrimidine were initially introduced into 15 ml of dry tetrahydrofuran, and 0.4 g (12 mmol) of sodium hydride (80% in mineral oil) was added in portions at room temperature. The mixture was subsequently stirred at room temperature for 8 hours, 2 ml of methanol were added dropwise and the mixture was concentrated. The residue was taken up in ethyl acetate, the mixture was filtered and the filtrate was concentrated. For purification, the residue was chromatographed over silica gel (petroleum ether/ethyl acetate 1:1).

Workup

  1. additionwas added in portions at room temperature
  2. concentrationthe mixture was concentrated
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customFor purification
  6. customthe residue was chromatographed over silica gel (petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-841cc2a712494ac8a656b65e51c5ad6d
Source dataset
uspto-grants-2001_08
Patent number
US06281221B1

Reaction notes

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