4-Phenoxyphenylboronic acid → (E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)-4-(dimethylamino)but-2-en-1-one

HRID 1522283Notes

Reaction equation

HRID 1522283 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:26][CH:27]1[CH2:30][C:29]2([CH2:34][CH2:33][N:32]([C:35]([O:37]C(C)(C)C)=O)[CH2:31]2)[CH2:28]1.Cl.[CH3:43][N:44]([CH3:51])[CH2:45]/[CH:46]=[CH:47]/C(O)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][CH:27]2[CH2:28][C:29]3([CH2:34][CH2:33][N:32]([C:35](=[O:37])/[CH:47]=[CH:46]/[CH2:45][N:44]([CH3:51])[CH3:43])[CH2:31]3)[CH2:30]2)[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 56962195tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 71092925(E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)-4-(dimethylamino)but-2-en-1-oneYield 5.4%

Procedure

(E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)-4-(dimethylamino)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride with method S1, S2, S3, S4A. Yield 5.4%. 1H NMR (CD3OD) δ 8.31 (s, 1H), 7.10-7.47 (m, 9H), 6.75 (m, 2H), 3.97 (m, 2H), 3.65 (m, 1H), 3.50 (m, 1H), 2.92 (m, 6H), 2.38 (m, 2H), 2.12 (m, 2H), 2.0 (t, 1H), 1.80 (m, 2H), 1.62 (m, 2H). HPLC PURITY: 98%, MS: m/z=499[M+H]+

Sources & evidence

ORD record
ord-9aee8334a11f4a69bf2254fc4d304aa1
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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