4,6-Dichloro-5-nitropyrimidine → HCID 86665162, compound

HRID 1619437Notes

Reaction equation

HRID 1619437 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][O:3]1.[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21](Cl)[N:20]=[CH:19][N:18]=1.CC(N(C)C)=O>>[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([O:14][C:11]2[CH:12]=[CH:13][C:8]([CH:5]3[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][CH2:6]3)=[CH:9][CH:10]=2)[N:20]=[CH:19][N:18]=1

Participants

4

Reactant 3

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 31374DimethylacetamideHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenol

Product 1

HCID 86665162HCID 86665162, compoundYield 52.6%

Procedure

To a solution of 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (500 mg, 0.0026 moles) and 4,6 dichloro-5-nitropyrimidine (600 mg, 0.0028 mole) in dimethyl acetamide (10 ml) K2CO3 (776 mg, 0.00577 mole) was added −20° C. The reaction mixture was stirred for about 2 hours at −10° C. to −18° C. The reaction mixture was then poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield crude product which was purified by column chromatography using 15% ethyl acetate in hexane as eluent to yield 500 mg product as pale yellow solid.

Workup

  1. additionThe reaction mixture was then poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto yield crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1ecbc5f67724410cb7970b55a6ea871b
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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