Dimethyl Sulfoxide → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal

HRID 856005Notes

Reaction equation

HRID 856005 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C:17]2[CH:18]=[N:19][N:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][OH:35])=[CH:28][CH:27]=4)[CH:23]=[N:22][C:21]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([C:17]2[CH:18]=[N:19][N:20]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][CH:34]=[O:35])=[CH:30][CH:31]=4)[CH:23]=[N:22][C:21]=23)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 586915973-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol

Product 1

HCID 586916073-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dimethylsulfoxide (0.862 mL, 12.2 mmol, 5.00 equiv) was added to a solution of oxalyl chloride (0.636 mL, 7.29 mmol, 3.00 equiv) in dichloromethane (10 mL) at −78° C. The mixture was stirred for 15 minutes before a solution of 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol (2-4, 0.800 g, 2.43 mmol, 1 equiv) in dichloromethane (100 mL) was added via cannula over 5 minutes. The resulting mixture was stirred at −78° C. for 1 hour. Triethylamine (3.50 mL, 25.1 mmol, 10.3 equiv) was added, and the mixture was then warmed to 0° C. and stirred for 30 minutes. The reaction mixture was partitioned between saturated sodium bicarbonate solution (100 mL) and additional dichloromethane (100 mL). The organic layer was dried over sodium sulfate and concentrated to give 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal (2-5) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ9.86 (t, 1H, J=1.2 Hz), 8.82 (d, 1H, J=2.4 Hz), 8.81 (d, 1H, J=2.4 Hz), 8.46 (s, 1H), 8.06 (br d, 2H, J=7.8 Hz), 7.54 (d, 2H, J=8.2 Hz), 7.47 (t, 2H, J=7.8 Hz), 7.37 (d, 2H, J=8.2 Hz), 7.29 (t, 1H, J=7.8 Hz), 3.05 (t, 2H, J=7.1 Hz), 2.86 (t, 2H, J=7.1 Hz).

Workup

  1. additionwas added via cannula over 5 minutes
  2. temperaturethe mixture was then warmed to 0° C.
  3. stirringstirred for 30 minutes
  4. customThe reaction mixture was partitioned between saturated sodium bicarbonate solution (100 mL) and additional dichloromethane (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3ea09b485b4e5eabb19b041a8b9ff4
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

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