2,4-Dichloro-6-methyl-5-nitropyrimidine → HCID 57747345, compound

HRID 386638Notes

Reaction equation

HRID 386638 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([SH:19])=[C:14]([CH3:20])[CH:13]=1.[Cl:21][C:22]1[N:27]=[C:26]([CH3:28])[C:25]([N+:29]([O-:31])=[O:30])=[C:24](Cl)[N:23]=1>C1COCC1>[Br:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19][C:24]2[C:25]([N+:29]([O-:31])=[O:30])=[C:26]([CH3:28])[N:27]=[C:22]([Cl:21])[N:23]=2)=[C:14]([CH3:20])[CH:13]=1

Participants

5

Reactant 3

HCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 2733832Lithium HexamethyldisilazideHCID 577474204-Bromo-2,6-dimethylbenzenethiol

Product 1

HCID 57747345HCID 57747345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-100 °C

Procedure

A solution of LiHMDS in THF (77 mmol) is added to a mixture of 4-bromo-2,6-dimethylbenzenethiol (70 mmol) in THF (100 ml) at −78° C. over 15 minutes and the mixture stirred for an additional 2 hours. The mixture is cooled with liquid nitrogen to around −100° C. and a solution of 2,6-dichloro-4-methyl-5-nitropyrimidine (84 mmol) in THF (50 ml) is added rapidly. The reaction is maintained at around −100° C. for 1 hour and then allowed to warm to room temperature. The mixture is filtered and the isolated solid washed with ethanol. The filtrate may be concentrated and crystallized to obtain additional compound.

Workup

  1. temperatureThe reaction is maintained at around −100° C. for 1 hour
  2. temperatureto warm to room temperature
  3. filtrationThe mixture is filtered
  4. washthe isolated solid washed with ethanol
  5. concentrationThe filtrate may be concentrated
  6. customcrystallized
  7. customto obtain additional compound

Sources & evidence

ORD record
ord-91dbab3ffae04b1ebc8a535a746890c7
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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