2-Methyl-3-butyn-2-ol → 4-[1-(2-aminopyrimidin-4-yl)-2-ethoxy-1H-1,3-benzodiazol-6-yl]-2-methylbut-3-yn-2-ol

HRID 1398642Notes

Reaction equation

HRID 1398642 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH2:11][CH3:12])[N:7]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)[C:6]=2[CH:20]=1.[CH3:21][C:22]([OH:26])([C:24]#[CH:25])[CH3:23]>>[NH2:19][C:15]1[N:14]=[C:13]([N:7]2[C:6]3[CH:20]=[C:2]([C:25]#[C:24][C:22]([CH3:23])([OH:26])[CH3:21])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:10][CH2:11][CH3:12])[CH:18]=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 681818044-(6-Bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine

Product 1

HCID 601644084-[1-(2-aminopyrimidin-4-yl)-2-ethoxy-1H-1,3-benzodiazol-6-yl]-2-methylbut-3-yn-2-ol

Procedure

The title compound was prepared by the procedure described in Step 2 of Example 142-b by reacting 4-(6-bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine with 2-methyl-3-butyn-2-ol; 1H NMR (500 MHz, MeOD) delta 1.54 (3H, t, J=7.09 Hz), 1.58 (6H, s), 4.68 (2H, q, J=7.09 Hz), 7.11 (1H, d, J=5.67 Hz), 7.25-7.32 (1H, m), 7.39 (1H, d, J=8.20 Hz), 8.29 (1H, s), 8.31-8.43 (1H, m); LC-MS: m/z=+338.5 (M+H)+.

Sources & evidence

ORD record
ord-719738b989d74a6db832265713cc75a5
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…