Tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)azetidine-1-carboxylate → HCID 178452152, compound

HRID 2194571Notes

Reaction equation

HRID 2194571 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH:11]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:22][C@@H:23]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1>>[CH3:22][C@@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][C:5]2[N:4]=[C:3]([O:9][CH2:10][CH:11]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:2]([Br:1])=[CH:7][N:6]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 86761726Tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)azetidine-1-carboxylateHCID 178461304HCID 178461304, compound

Product 1

HCID 178452152HCID 178452152, compoundYield 55%

Procedure

Using the procedure of Example 1 Step 2, tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)azetidine-1-carboxylate was reacted with cis-4-methylcyclohexanamine to provide the title compound in 55% yield. 1H NMR (CDCl3, 300 MHz) 8.10 (s, 1H), 5.17 (m, 1H), 5.47 (d, 2H), 4.11-4.00 (m, 3H), 3.84-3.79 (m, 2H), 3.02-2.98 (m, 1H), 1.78-1.58 (m, 6H), 1.46 (s, 9H), 1.46-1.27 (m, 3H), 0.95 (d, 3H); MS (ESI) m/z: Calc: 454.2 (M+). Found. 456.1 (M+2).

Sources & evidence

ORD record
ord-8bafd5f60ad44fe0a3752ae0cb98557d
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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