Sodium Carbonate → HCID 57965012, compound

HRID 1931596Notes

Reaction equation

[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH:12]([NH:15][NH2:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:17][C:18]1[C:23]([CH:24]=O)=[C:22](Cl)[N:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:17][C:18]1[N:19]=[CH:20][N:21]=[C:22]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:10][CH2:11]3)[N:16]=[CH:24][C:23]=12

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of [4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-hydrazine (Intermediate 12; 230 mg, 1.0 mmol), 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16; 182 mg, 1.0 mmol) and sodium carbonate (218 mg, 2.1 mmol) in acetonitrile was heated in the microwave at 140° C. for 10 min. Saturated aqueous sodium carbonate was added and the reaction mixture was filtered. The filtrate was extracted with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 10% ethyl acetate/hexanes to give 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (125 mg, 35%) as a white solid. Mass spectrum M+=346.

Workup

filtrationthe reaction mixture was filtered
extractionThe filtrate was extracted with ethyl acetate
dry with materialthe combined organic layers were dried (sodium sulfate)
filtrationfiltered
customevaporated
custompurified by flash chromatography
washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-0fdd78d6ab674a2dbd81a5c03cbed1c8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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