Dimethylamine → 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine

HRID 2357659Notes

Reaction equation

[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[C:6]([O:12][CH3:13])=[N:7][C:8](Cl)=[N:9][CH:10]=1>>[Br:4][C:5]1[C:6]([O:12][CH3:13])=[N:7][C:8]([N:2]([CH3:3])[CH3:1])=[N:9][CH:10]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 6158295-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amineYield 98.2%

Conditions

Temperature: 45 °C

Procedure

A solution of dimethylamine (2.0 M solution in THF, 17.2 mL, 34.5 mmol) was added to 5-bromo-2-chloro-4-methoxypyrimidine (1.540 g, 6.89 mmol) at RT. The reaction was heated to 45° C. for 30 min, then cooled and concentrated. The residue was washed and filtered with diethyl ether to give 1.57 g of 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine as a light yellow solid. ES+=232.0 (M+H)

Workup

temperaturecooled
concentrationconcentrated
washThe residue was washed
filtrationfiltered with diethyl ether

Sources & evidence

ORD record: ord-14e03286722344c0b75b5b4c102047d8
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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