Dimethylformamide → HCID 86698465, compound

HRID 527679Notes

Reaction equation

HRID 527679 reaction equation
[C:1]12([C:12]3[C:11]([OH:13])=[CH:10][CH:9]=[CH:8][C:7]=3[O:6][CH2:5][CH2:4]1)[CH2:3][CH2:2]2.CN(C=O)C.Cl[C:20]1[N:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1>>[C:1]12([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[O:13][C:20]3[N:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=3)[O:6][CH2:5][CH2:4]1)[CH2:3][CH2:2]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 825442-Chloro-5-nitropyrimidineHCID 86698464HCID 86698464, compound2×

Product 1

HCID 86698465HCID 86698465, compoundYield 84.9%

Procedure

To a solution of 2,3-dihydrospiro[chromene-4,1′-cyclopropan]-5-ol (Intermediate 221, 63 mg, 0.358 mmol) in DMF (3 ml) K2CO3 (74.1 mg, 0.536 mmol) and 2-chloro-5-nitropyrimidine (86.0 mg, 0.536 mmol) were added and the reaction mixture was stirred at rt for 1 h. DMF was then evaporated under high vacuum, water was added and the reaction mixture was extracted with AcOEt (three times). Collected organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents affording the title compound (91 mg).

Workup

  1. customDMF was then evaporated under high vacuum, water
  2. additionwas added
  3. extractionthe reaction mixture was extracted with AcOEt (three times)
  4. dry with materialCollected organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (Biotage system) on silica gel

Sources & evidence

ORD record
ord-99670e8dd9194f3ca3986ced554eb28e
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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