4-Phenoxyphenylboronic acid → (E)-1-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)-4-(dimethylamino)but-2-en-1-one

HRID 1522193Notes

Reaction equation

HRID 1522193 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.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.[CH3:42][N:43]([CH3:50])[CH2:44]/[CH:45]=[CH:46]/C(O)=O>>[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:46]=[CH:45]/[CH2:44][N:43]([CH3:50])[CH3:42])[CH2:16]3)[CH2:24]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 71092970(E)-1-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)-4-(dimethylamino)but-2-en-1-one

Procedure

(E)-1-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)-4-(dimethylamino)but-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-hydroxyl-2-azaspiro[3.3]heptane-2-carboxylate, (4-phenoxyphenyl)boronic acid and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 99%. MS: m/z=486 [M+H]+. 1H NMR (CD3OD) δ 8.28 (s, 1H), 7.18-7.45 (m, 9H), 6.63 (m, 1H), 6.45 (dd, 1H), 5.25 (m, 1H), 4.32 (d, 2H), 4.13 (d, 2H), 4.92 (t, 2H), 3.81 (m, 6H), 2.74 (m, 2H), 2.23 (m, 2H).

Sources & evidence

ORD record
ord-c0118aeef7ed4279ac0b78bfa97875b8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

Loading…