Propiolic Acid → 1-(6-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)prop-2-yn-1-one

HRID 1522199Notes

Reaction equation

HRID 1522199 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[CH2:10]([N:17]1[CH:21]=[C:20](B(O)O)[CH:19]=[N:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:25][CH:26]1[CH2:39][C:28]2([CH2:31][N:30]([C:32]([O:34]C(C)(C)C)=O)[CH2:29]2)[CH2:27]1.[C:40](O)(=O)[C:41]#C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:25][CH:26]2[CH2:27][C:28]3([CH2:29][N:30]([C:32](=[O:34])[C:40]#[CH:41])[CH2:31]3)[CH2:39]2)[C:2]=1[C:20]1[CH:19]=[N:18][N:17]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:21]=1

Participants

5

Reactant 4

HCID 10110Propiolic AcidHCID 33528811-Benzyl-1H-pyrazole-4-boronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 867217971-(6-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)prop-2-yn-1-one

Procedure

1-(6-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)prop-2-yn-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (1-benzyl-1H-pyrazol-4-yl)boronic acid, tert-butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate and propiolic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 95%. MS: m/z=414 [M+H]+. 1H NMR (CD3OD) δ 8.21 (s, 1H), 7.83 (s, 1H), 7.57 (s, 1H), 7.41 (m, 5H), 5.42 (s, 2H), 4.54 (s, 1H), 4.31 (d, 2H), 4.08 (d, 2H), 3.88 (d, 1H), 2.61 (m, 2H), 2.30 (m, 2H).

Sources & evidence

ORD record
ord-cc2cbba8debd4ceeb5dc4b5697162f72
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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