Acrylic 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-en-1-one

HRID 1522195Notes

Reaction equation

HRID 1522195 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.[CH2:25]([N:32]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:40](O)(=O)[CH:41]=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])[CH:40]=[CH2:41])[CH2:16]3)[CH2:24]2)[C:2]=1[C:35]1[CH:34]=[N:33][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:36]=1

Participants

5

Reactant 4

HCID 6581Acrylic 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 867217941-(6-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-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-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate, (1-benzyl-1H-pyrazol-4-yl)boronic acid and acrylic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 98%. MS: m/z=416 [M+H]+. 1H NMR (CD3OD) δ 8.21 (s, 1H), 7.84 (s, 1H), 7.58 (s, 1H), 7.41 (m, 5H), 6.29 (m, 2H), 5.72 (m, 1H), 5.43 (s, 2H), 4.56 (s, 1H), 4.34 (d, 2H), 4.10 (d, 2H), 2.58 (m, 2H), 2.27 (m, 2H).

Sources & evidence

ORD record
ord-f0a01cc21cad47208767541982d53150
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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