5-Bromo-2,4-dichloropyrimidine → (R)-tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylate

HRID 2194564Notes

Reaction equation

HRID 2194564 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][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1>>[Br:1][C:2]1[C:3]([O:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86761725(R)-tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylate

Procedure

Using the procedure of Example 1 Step 1, 5-bromo-2,4-dichloropyrimidine was reacted with (R)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.42 (s, 1H), 4.10 (m, 2H), 3.62-3.17 (m, 5H), 2.72-2.69 (m, 1H), 2.10-2.05 (m, 2H), 1.80-1.75 (m, 1H), 1.44 (s, 9H); MS (ESI) m/z: Calc: 392.68 (M). Found. 337.9 (M+-(CH3)3C).

Sources & evidence

ORD record
ord-ddd212255e454d11833dde6804b8e322
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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