Potassium Carbonate → 1-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-4-(2-methyl-pyridin-3-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931740Notes

Reaction equation

HRID 1931740 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][CH:14]([C:17]4[O:21][N:20]=[C:19]([CH:22]([CH3:24])[CH3:23])[N:18]=4)[CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12.[OH:25][C:26]1[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH:22]([C:19]1[N:18]=[C:17]([CH:14]2[CH2:15][CH2:16][CH:11]([N:8]3[C:4]4=[N:5][CH:6]=[N:7][C:2]([O:25][C:26]5[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=5)=[C:3]4[CH:10]=[N:9]3)[CH2:12][CH2:13]2)[O:21][N:20]=1)([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 707192-Methylpyridin-3-olHCID 57965012HCID 57965012, compound2×

Product 1

HCID 579648861-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-4-(2-methyl-pyridin-3-yloxy)-1H-pyrazolo[3,4-d]pyrimidineYield 76%

Procedure

1-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-4-(2-methyl-pyridin-3-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (60 mg, 76%) was prepared using the procedure described for the preparation of Example 41 by the reaction of 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 23; 130 mg, 0.375 mmol) with 3-hydroxy-2-methylpyridine (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA; 42 mg, 0.385 mmol) in the presence of potassium carbonate (114 mg, 0.825 mmol). The compound was purified by column chromatography, eluting with 5% methanol/dichloromethane. Mass spectrum MH+=420.

Workup

  1. customThe compound was purified by column chromatography
  2. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-257b1a7f595f474e9dedd4d2e25d9780
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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