Cesium carbonate → Pf-04447943

HRID 2424827Notes

Reaction equation

Cl.[CH3:2][C@@H:3]1[CH2:7][NH:6][CH2:5][C@H:4]1[C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:12]=2[N:13]=1.Cl.Cl[CH2:26][C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[O-]S(C(F)(F)F)(=O)=O.[Fe+2].[O-]S(C(F)(F)F)(=O)=O>[CH3:2][C@@H:3]1[CH2:7][N:6]([CH2:26][C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:5][C@H:4]1[C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:12]=2[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride (7.75 g) (see preparation in step (a) of Example 73) in dimethylformamide (115 mL) was added iron triflate (900 mg), 2-(chloromethyl)pyrimidine hydrogen chloride (4.5 g), and cesium carbonate (22.2 g) and the reaction mixture was heated at 60° C. for 24 h. The reaction mixture was concentrated onto silica gel and purified by flash chromatography eluting with 0-15% methanoylethyl acetate/1% saturated ammonium hydroxide to provide the title compound (6 g). 400 MHz 1H NMR (CDCl3) δ 12.30 (brs, 1H), 8.63 (d, J=5.0, Hz, 2H), 8.03 (s, 1H). 7.20 (d, J=5.0, Hz, 1H), 4.84-4.79 (m, 1H), 4.30-4.27 (m, 1H), 4.14-4.08 (m, 2H), 3.87-3.82 (m, 1H), 3.63-3.55 (m, 2H), 3.47 (t, J=7.9 Hz, 1H), 3.29 (d, J=9.9 Hz, 1H), 2.88-2.86 (m, 1H), 2.60-2.56 (m, 1H), 2.46-2.24 (m, 4H), 1.93-1.84 (m, 2H), 1.24 (t, J=7.1 Hz, 3H). MS: (M+H m/z 396.2).

Workup

concentrationThe reaction mixture was concentrated onto silica gel
custompurified by flash chromatography
washeluting with 0-15% methanoylethyl acetate/1% saturated ammonium hydroxide

Sources & evidence

ORD record: ord-c7f243349f6845a88c307e906e19e26b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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