Stannanecarbonitrile, tributyl- → HCID 131731056, compound

HRID 2047169Notes

Reaction equation

Br[C:2]1[C:3]([N:40]2[CH2:45][CH2:44][S:43][CH2:42][CH2:41]2)=[N:4][C:5]2[N:6]([N:25]=[CH:26][C:27]=2[CH:28]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:39])[C:7]=1[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].[Sn]([C:59]#[N:60])(CCCC)(CCCC)CCCC>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:7]1[N:6]2[N:25]=[CH:26][C:27]([CH:28]3[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:39])=[C:5]2[N:4]=[C:3]([N:40]2[CH2:45][CH2:44][S:43][CH2:42][CH2:41]2)[C:2]=1[C:59]#[N:60]

Participants

Conditions

Temperature: 100 °C

Procedure

A degassed mixture of 6-bromo-5-thiomorpholinodioxo-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (35 mg, 0.051 mmoL), Bu3SnCN (32.3 mg, 0.10 mmoL), Pd[P(t-Bu)3]2 (5.2 mg, 0.010 mmoL) in Dioxane (3 mL) was heated at 100° C. overnight. The mixture was cooled to room temperature and the solvent was evaporated. Purification by column chromatography afforded 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-5-thiomorpholinodioxo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile. LCMS tR=2.76 Min (5 min run, UV254nm). Mass calculated for, M+ 678.28, observed LC/MS m/z 679.20 (M+H).

Workup

temperatureThe mixture was cooled to room temperature
customthe solvent was evaporated
customPurification by column chromatography

Sources & evidence

ORD record: ord-8dd6d6f2556c44fcb9d8ec89291e4158
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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