Potassium Carbonate → HCID 57961794, compound

HRID 541915Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:18][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][OH:17])[CH:10]=2)=[N:7][C:2]([NH:19][C:20]2[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethanol (0.10 g, 0.35 mmol) and 3-aminophenol (58 mg, 0.53 mmol) in 1,4-dioxane (3.5 mL) was treated with p-toluenesulfonic acid monohydrate (54 mg, 0.28 mmol) and heated at 100° C. for 1 h. The reaction mixture was treated with additional 3-aminophenol (19 mg, 0.18 mmol) and heated at 100° C. for 1 h. The reaction mixture was poured into 10% potassium carbonate (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude brown oil. This material was purified by flash column chromatography to give the desired product (0.12 g, 96%) as a light brown solid. LCMS for C18H18ClN4O2 (M+H)+: m/z=357.0.

Workup

temperatureheated at 100° C. for 1 h
extractionextracted with ethyl acetate (2×50 mL)
washThe combined organic layers were washed with brine (25 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated to a crude brown oil
customThis material was purified by flash column chromatography

Sources & evidence

ORD record: ord-c91c1d26352e4f9ea9a8867c387134a0
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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