2-Butynoic acid → 1-(6-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)but-2-yn-1-one

HRID 1522196Notes

Reaction equation

HRID 1522196 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:24][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.[C:41](O)(=O)[C:42]#[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([CH2:14][N:15]([C:17](=[O:19])[C:41]#[C:42][CH3:43])[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 685352-Butynoic acidHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 710930511-(6-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)but-2-yn-1-one

Procedure

1-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)but-2-yn-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate, (4-phenoxyphenyl)boronic acid and but-2-ynoic 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 8.24 (s, 1H), 7.16-7.45 (m, 9H), 4.57 (s, 1H), 4.27 (d, 2H), 4.05 (d, 2H), 2.61 (m, 2H), 2.27 (m, 2H), 2.00 (m, 3H).

Sources & evidence

ORD record
ord-1346fdf5530c440f9b2d2362e10b9d02
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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