2-Chlorobenzaldehyde → HCID 69154601, compound

HRID 2251956Notes

Reaction equation

HRID 2251956 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[N:14][CH:15]=1.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>CCOCC>[Br:9][C:10]1[C:11]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[Cl:16])[OH:20])=[N:12][CH:13]=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 783445-BromopyrimidineHCID 2724682Lithium diisopropylamide

Product 1

HCID 69154601HCID 69154601, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Slowly add freshly prepared lithium diisopropylamide (0.5 M in ether) to a refluxing solution of 5-bromopyrimidine (4.03 g, 25.3 mmol) and 2-chloro-benzaldehyde (3.55 g, 25.2 mmol) in ether (100 mL). After addition is complete, stir at reflux for an additional 2 hours, then quench with 2N HCl (50 mL). Wash the organic layer with water (4×50 mL), dry, filter, and concentrate. Purify the crude material by flash chromatography using a linear gradient of 100% hexanes to 50% EtOAc/hexanes to give the title compound: MS (IS) 298.9 (M+1); 1H NMR (400 MHz, CDCl3) δ 9.19 (s, 1H), 8.77 (s, 1H), 7.40 (dd, 1H, J=1.4, 8.4), 7.23 (dt, 1H, J=1.9, 7.9), 7.15 (dt, 1H, J=1.4, 7.7), 6.92 (dd, 1H, J=1.5,7.9), 6.34 (d, 1H, J=6.4), 4.75 (d, 1H, J=6.7).

Workup

  1. additionAfter addition
  2. temperatureat reflux for an additional 2 hours
  3. customquench with 2N HCl (50 mL)
  4. washWash the organic layer with water (4×50 mL)
  5. customdry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-567146a8050e4b67a51b913df1fd8e37
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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