Acrylic Acid → 1-(6-((6-Amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-1-one

HRID 1522201Notes

Reaction equation

HRID 1522201 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.[N:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)=[CH:27][CH:26]=1.[C:41](O)(=O)[CH:42]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:10][CH:11]2[CH2:12][C:13]3([CH2:14][N:15]([C:17](=[O:19])[CH:41]=[CH2:42])[CH2:16]3)[CH2:24]2)[C:2]=1[C:35]1[CH:36]=[CH:37][C:32]([O:31][C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 6581Acrylic AcidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylateHCID 576553424-(Pyridin-4-yloxy)phenylboronic acid

Product 1

HCID 867218001-(6-((6-Amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-1-one

Procedure

1-(6-((6-amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-hydroxyl-2-azaspiro[3.3]heptane-2-carboxylate, (4-(pyridin-4-yloxy)phenyl)boronic acid and acrylic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 99%. MS: m/z=430 [M+H]+. 1H NMR (CD3OD) δ 8.75 (m, 2H), 8.31 (m, 1H), 7.56 (m, 4H), 7.44 (m, 2H), 6.27 (m, 1H), 5.73 (m, 1H), 5.24 (m, 1H), 4.26 (d, 2H), 4.01 (d, 2H), 2.73 (m, 2H), 2.25 (m, 2H).

Sources & evidence

ORD record
ord-36d9fdd5da0e41a99efb0ce33b17088a
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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