Propargyl alcohol → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol

HRID 856003Notes

Reaction equation

HRID 856003 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=2)=[CH:4][CH:3]=1.[CH2:23]([OH:26])[C:24]#[CH:25]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([C:16]2[CH:15]=[N:14][N:12]3[CH:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([C:25]#[C:24][CH2:23][OH:26])=[CH:3][CH:4]=4)[CH:9]=[N:10][C:11]=23)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 586916066-(4-Bromophenyl)-3-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 586916053-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Procedure

A deoxygenated mixture of 6-(4-bromophenyl)-3-phenylpyrazolo[1,5-a]pyrimidine (2-2, 3.00 g, 8.57 mmol, 1 equiv), propargyl alcohol (1.50 mL, 25.8 mmol, 3.01 equiv), and tetrakis(triphenylphosphine)palladium (0.500 g, 0.433 mmol, 0.050 equiv) in pyrrolidine (50 mL) was heated at reflux for 2.5 hours. The reaction mixture was concentrated, and the residue was suspended in methanol (50 mL) and filtered to give 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol (2-3) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ9.56 (d, 1H, J=2.4 Hz), 9.07 (d, 1H, J=2.2 Hz), 8.82 (s, 1H), 8.18 (br d, 2H, J=7.8 Hz), 7.92 (d, 2H, J=8.2 Hz), 7.58 (d, 2H, J=8.2 Hz), 7.46 (t, 2H, J=7.8 Hz), 7.27 (t, 1H, J=7.8 Hz), 5.37 (t, 1H, J=6.0 Hz), 4.35 (d, 2H, J=6.0 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b89e64de025948e89a31e590f5580be9
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

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