5-Bromo-2,4-dichloropyrimidine → Tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)azetidine-1-carboxylate

HRID 2194570Notes

Reaction equation

HRID 2194570 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH:10][CH2:11][CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1>>[Br:1][C:2]1[C:3]([O:10][CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 86761726Tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)azetidine-1-carboxylateYield 67%

Procedure

Using the procedure of Example 1 Step 1, 5-bromo-2,4-dichloropyrimidine was reacted with tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate to provide the title compound at 67% yield. 1H NMR (CDCl3, 400 MHz) 8.46 (s, 1H), 4.61 (d, 2H), 4.10 (m, 2H), 3.82 (m, 2H), 3.03 (m, 1H), 1.45 (9H); MS (ESI) m/z: Calc: 377.0 (M+). Found. 322.9 (M+-(CH3)3C+1).

Sources & evidence

ORD record
ord-bf401e1129f3415487a3bda08f2e55c4
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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