HCID 58169125, compound → 3-(tert-butyldimethylsilyloxy)-3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propyl acetate
Reaction equation
ClC1C(NC2C=C(C3CC3)NN=2)=NC(C2SC(C(O)C(OCC)=O)=CC=2)=NC=1.[C:29]([O:32][CH2:33][CH2:34][CH:35]([C:44]1[S:45][C:46](Br)=[CH:47][CH:48]=1)[O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=[O:31])[CH3:30].C(OCCC(C1SC(B(O)O)=CC=1)O[Si](C(C)(C)C)(C)C)(=O)C.Br[C:74]1[N:79]=[C:78]([NH:80][C:81]2[CH:85]=[C:84]([CH:86]3[CH2:88][CH2:87]3)[NH:83][N:82]=2)[C:77]([C:89]#[C:90][Si](C)(C)C)=[CH:76][N:75]=1>>[C:29]([O:32][CH2:33][CH2:34][CH:35]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C:44]1[S:45][C:46]([C:74]2[N:79]=[C:78]([NH:80][C:81]3[CH:85]=[C:84]([CH:86]4[CH2:88][CH2:87]4)[NH:83][N:82]=3)[C:77]([C:89]#[CH:90])=[CH:76][N:75]=2)=[CH:47][CH:48]=1)(=[O:31])[CH3:30]Participants
5
Reactant 4
Product 1
Procedure
Following procedure from Compound 191, 3-(5-Bromothiophen-2-yl)-3-(tert-butyldimethylsilyloxy)propyl acetate was converted to 5-(3-acetoxy-1-(tert-butyldimethylsilyloxy)propyl)thiophen-2-ylboronic acid (2.7 g, 94.5%) (LC-MS (m/z)=441.0 [M+H]+), which was condensed with 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine to produce 3-(tert-butyldimethylsilyloxy)-3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propyl acetate (500 mg, 50.0%). LC-MS (m/z)=538.1 [M+H]+
Sources & evidence
- ORD record
- ord-f2ecd5a280de45c8852295772ed164ba
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422271B2
Reaction notes
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