Azetidine → HCID 117820981, compound

HRID 59087Notes

Reaction equation

HRID 59087 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[C:11]([CH2:16][O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[N:10]=1>C(#N)C>[N:1]1([C:13]2[CH:12]=[C:11]([CH2:16][O:17][CH2:18][CH:19]3[CH2:20][CH2:21]3)[N:10]=[C:9]([Cl:8])[N:14]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 10942334Sodium MethoxideHCID 117821043HCID 117821043, compound

Product 1

HCID 117820981HCID 117820981, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of azetidine (93 mg, 0.99 mmol) and sodium methoxide (30 wt % in methanol, 0.135 mL, 0.73 mmol) in acetonitrile (6 mL) was added 2,4-dichloro-6-((cyclopropylmethoxy)-methyl)pyrimidine (77 mg, 0.33 mmol). The reaction was stirred at rt for 30 minutes. The mixture was purified by preparative HPLC to give the title compound (44 mg, 53%).

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-bf60560231694175ad13fda93c5e91f9
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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