Acryloyl chloride → 4-(4-(4-((2-Acryloyl-2-azaspiro[3.3]heptan-6-yl)oxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile
Reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[OH:10][CH:11]1[CH2:24][C:13]2([CH2:16][N:15]([C:17]([O:19]C(C)(C)C)=O)[CH2:14]2)[CH2:12]1.CC1(C)C(C)(C)OB([C:33]2[CH:47]=[CH:46][C:36]([O:37][C:38]3[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=3)=[CH:35][CH:34]=2)O1.[C:49](Cl)(=O)[CH:50]=C>>[C:17]([N:15]1[CH2:14][C:13]2([CH2:12][CH:11]([O:10][C:7]3[C:2]([C:33]4[CH:47]=[CH:46][C:36]([O:37][C:38]5[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=5)=[CH:35][CH:34]=4)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=3)[CH2:24]2)[CH2:16]1)(=[O:19])[CH:49]=[CH2:50]Participants
5
Reactant 4
Product 1
Procedure
4-(4-(4-((2-acryloyl-2-azaspiro[3.3]heptan-6-yl)oxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate, 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods A, C, D, and F. HPLC: 100%. MS: m/z=454 [M+H]+.
Sources & evidence
- ORD record
- ord-53fcf2c029484597a8076e3a5789accc
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073947B2
Reaction notes
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