2-Chloro-5-nitropyrimidine → HCID 58386134, compound

HRID 1963034Notes

Reaction equation

HRID 1963034 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.Cl[C:9]1[N:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1>>[CH3:1][NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:9]2[N:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 825442-Chloro-5-nitropyrimidineHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidine

Product 1

HCID 58386134HCID 58386134, compound

Conditions

Temperature
110 °C

Procedure

(S)—N-Methylpyrrolidin-3-amine (286 mg, 2.86 mmol) was added to 2-chloro-5-nitropyrimidine (415 mg, 2.60 mmol) slowly (CAUTION: extreme exotherm!!!). The resulting mixture was heated at 110° C. for 10 min. After cooling down to room temperature, another portion of amine (0.100 g) was added to the reaction mixture. The resulting mixture was heated at 110° C. for 10 min. After cooling down to room temperature, the obtained black solid product (Example 47A) was used for next step without further purification. LCMS (ES): m/z 252.3 [M+H]+.

Workup

  1. temperatureAfter cooling down to room temperature
  2. temperatureThe resulting mixture was heated at 110° C. for 10 min
  3. temperatureAfter cooling down to room temperature
  4. customthe obtained black solid product (Example 47A) was used for next step without further purification

Sources & evidence

ORD record
ord-d5de1f7c0ccc4cfc95147f1709f82645
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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