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

HRID 222082Notes

Reaction equation

HRID 222082 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-15dc404474e34327ad81669b546da166
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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