Potassium Carbonate → HCID 178434705, compound

HRID 1931738Notes

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1.Cl[C:15]1[N:20]=[CH:19][N:18]=[C:17]2[N:21]([C@H:24]3[CH2:29][CH2:28][C@H:27]([C:30]4[O:34][N:33]=[C:32]([CH:35]([CH3:37])[CH3:36])[N:31]=4)[CH2:26][CH2:25]3)[N:22]=[CH:23][C:16]=12.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:35]([C:32]1[N:31]=[C:30]([C@H:27]2[CH2:28][CH2:29][C@H:24]([N:21]3[C:17]4=[N:18][CH:19]=[N:20][C:15]([O:13][C:10]5[CH:11]=[CH:12][C:7]([N:6]6[C:2]([CH3:1])=[N:3][N:4]=[N:5]6)=[CH:8][CH:9]=5)=[C:16]4[CH:23]=[N:22]3)[CH2:25][CH2:26]2)[O:34][N:33]=1)([CH3:37])[CH3:36]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-(5-methyl-tetrazol-1-yl)-phenol (Chembridge Corporation, San Diego, Calif., USA; 76 mg, 0.43 mmol), 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-trans-cyclo-hexyl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 26; 150 mg, 0.43 mmol), and potassium carbonate (72 mg, 0.52 mmol) in dimethylformamide (5 mL) was heated in a microwave at 180° C. for 10 min. The mixture was filtered. The filtrate was concentrated and purified using a Supelco 23 g column, eluting with 0-3% methanol/dichloromethane to give 1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-trans-cyclohexyl]-4-[4-(5-methyl-tetrazol-1-yl)-phenoxy]-1H-pyrazolo[3,4-d]pyrimidine (86 mg, 41%).

Workup

filtrationThe mixture was filtered
concentrationThe filtrate was concentrated
custompurified
washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record: ord-fd6983a2d17444d79d3a9902b9bde227
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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