Allyl Alcohol → 7-Allyloxy-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

HRID 348035Notes

Reaction equation

HRID 348035 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:27]([OH:30])[CH:28]=[CH2:29]>>[CH2:27]([O:30][C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[C:6]2[N:5]=[CH:4][CH:3]=1)[CH:28]=[CH2:29]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 21083723HCID 21083723, compound

Product 1

HCID 102501247-Allyloxy-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

Procedure

To a suspension of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine (I-13A-1a; 30 mg, 0.08 mmol) in allyl alcohol (0.8 ml) was added NaH (60% dispersion in oil, 2 mg, 0.08 mmol). After stirring overnight, the reaction was concentrated and purified on a Chromatotron using methylene chloride as eluant to give product 13A-1 (12 mg, 38%) as a solid: +ESI MS (M+1) 396.4; 1H NMR (400 MHz, CD3OD) δ 8.51 (d, J=5.4 Hz, 1H), 7.53–7.40 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 6.68 (d, J=5.4 Hz, 1H), 6.20 (ddt, J=17.0, 10.4, 5.8 Hz, 1H), 5.64–5.58 (m, 1H), 5.45–5.41 (m, 1H), 5.10–5.08 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified on a Chromatotron
  3. customto give product 13A-1 (12 mg, 38%) as a solid

Sources & evidence

ORD record
ord-d420502d2f79469f8934c0e08676cbd3
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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