Acryloyl chloride → 1-[4-[[(6-Amino-2'-phenoxy[5,5'-bipyrimidin]-4-yl)amino]methyl]-1-piperidinyl]-2-propen-1-one

HRID 1522234Notes

Reaction equation

HRID 1522234 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[O:25]([C:32]1[N:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][N:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:47](Cl)(=O)[CH:48]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18](=[O:20])[CH:47]=[CH2:48])[CH2:16][CH2:17]2)[C:2]=1[C:35]1[CH:36]=[N:37][C:32]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:33][CH:34]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 223468822-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 714745871-[4-[[(6-Amino-2'-phenoxy[5,5'-bipyrimidin]-4-yl)amino]methyl]-1-piperidinyl]-2-propen-1-one

Procedure

1-(4-(((6-amino-2′-phenoxy-[5,5′-bipyrimidin]-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine, and acryloyl chloride using methods B, C, D, and F. MS: m/z=432 [M+H]+. 1H NMR (400 MHz, DMSO) δ 8.37 (s, 2H), 7.96 (s, 1H), 7.47 (t, 2H), 7.30-7.20 (m, 3H), 6.76 (dd, 1H), 6.10-5.97 (m, 2H), 5.80 (s, 2H), 5.62 (dd, 1H), 4.35 (d, 1H), 3.99 (d, 1H), 3.10 (t, 2H), 3.02-2.89 (m, 1H), 2.56 (m, 1H), 1.81 (m, 1H), 1.63 (d, 2H), 1.02-0.83 (m, 2H).

Sources & evidence

ORD record
ord-6bdd647b3ce24e61a6e9386d6ade8992
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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