Propiolic Acid → 1-(2-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)prop-2-yn-1-one

HRID 1522202Notes

Reaction equation

HRID 1522202 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:14][C:13]2([CH2:18][CH2:17][N:16]([C:19]([O:21]C(C)(C)C)=O)[CH2:15]2)[CH2:12]1.[O:26]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:42](O)(=O)[C:43]#C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH:11]2[CH2:12][C:13]3([CH2:18][CH2:17][N:16]([C:19](=[O:21])[C:42]#[CH:43])[CH2:15]3)[CH2:14]2)[C:2]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 10110Propiolic AcidHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 56962195tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 867218011-(2-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)prop-2-yn-1-one

Procedure

1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)prop-2-yn-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate, (4-phenoxyphenyl)boronic acid and propiolic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 99%. MS: m/z=440 [M+H]+. 1H NMR (CD3OD) δ 8.01 (s, 1H), 7.12-7.48 (m, 9H), 4.52 (t, 1H), 3.71 (t, 1H), 3.58 (s, 1H), 3.50 (dd, 1H), 2.33 (m, 2H), 2.05 (m, 2H), 1.96 (m, 2H), 1.47 (s, 2H).

Sources & evidence

ORD record
ord-26aa870984a346769dfdd693f427be98
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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