5-Bromo-2,4-dichloropyrimidine → 5-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[O:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1>>[Br:1][C:2]1[C:3]([NH:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidine

HCID 4192234-Aminotetrahydropyran

Product 1

HCID 595508905-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amineYield 83%

Procedure

In the reaction of 5-bromo-2,4-dichloropyrimidine (300 mg, 1.32 mmol) with tetrahydropyran-4-ylamine (144 mg, 1.42 mmol) according to procedure 2, the desired product is obtained in 83% yield (320 mg) after chromatographic purification (silica gel, ethyl acetate/hexane with ethyl acetate: 0-100%).

Sources & evidence

ORD record: ord-d32b386aec14496bbfb7a1779e94f5b1
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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