Morpholine → HCID 58173399, compound

HRID 2368985Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.C(N(CC)C(C)C)(C)C.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>CN1C(=O)CCC1>[O:50]1[CH2:51][CH2:52][N:47]([C:2]2[CH:7]=[C:6]([NH2:8])[N:5]3[N:25]=[CH:26][C:27]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:4]3[N:3]=2)[CH2:48][CH2:49]1

Participants

Conditions

Temperature: 185 °C

Procedure

A mixture of 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (72 μmol, 40 mg), N,N-diisopropylethylamine (220 μmol, 38 μL), NMP (2 mL), and morpholine (220 μmol, 19 μL) was heated to 185° C. in microwave synthesizer for 45 minutes. Upon completion, the reaction was cooled to room temperature and then purified via prep-LC to yield 5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as brown-yellow solid. LCMS tR=1.29 Min (5 min run, UV254nm). Mass calculated for, M+ 346.1, observed LC/MS m/z 347.2 (M+H).

Workup

temperatureUpon completion, the reaction was cooled to room temperature
custompurified via prep-LC

Sources & evidence

ORD record: ord-25c03f02259c44868c0fb4cc1037f9e3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703784B2

Reaction notes

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