Isopropanol → HCID 11304101, compound

HRID 915858Notes

Reaction equation

HRID 915858 reaction equation
[Na].Cl[C:3]1[C:4]2[C:5](=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:11]=2)[N:6]=[CH:7][N:8]=1.[CH3:26][CH:27]([OH:29])[CH3:28]>>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2[N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:11]=[C:4]3[C:3]([O:29][CH:27]([CH3:28])[CH3:26])=[N:8][CH:7]=[N:6][C:5]=23)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 5360545SodiumHCID 58959477HCID 58959477, compound

Product 1

HCID 11304101HCID 11304101, compound

Conditions

Temperature
65 °C

Procedure

Sodium (21 mg, 0.9 mmol) was added to 2-propanol (2 ml), and the resultant mixture was stirred at 65° C. for 16 hours. Next, 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine I-2A-1c (75 mg, 0.2 mmol) was added in one portion, and the mixture was stirred at 65° C. for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. Purification of the residue by flash column chromatography (50% ethyl acetate in hexanes) provided the title compound 3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-isopropoxy-2H-pyrazolo[4,3-d]pyrimidine 8A-1 (41 mg): MS: 399.1 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 8.6 (s, 1H), 7.6 (d, J=6.6 Hz, 1H), 7.5 (m, 5H), 7.3 (d, J=8.7 Hz, 2H), 5.8 (pentuplet, J=6.2 Hz, 1H), 1.5 (d, J=6.2 Hz, 6H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customPurification of the residue by flash column chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-36cef2b6b01c42a0ac88d8c13d36b07b
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

Loading…