Ammonia → 2-Chloro-5-nitropyrimidin-4-amine

HRID 510157Notes

Reaction equation

HRID 510157 reaction equation
N.C([N:5](CC)C(C)C)(C)C.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1>ClCCl>[Cl:11][C:12]1[N:17]=[C:16]([NH2:5])[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 747162-Chloro-5-nitropyrimidin-4-amineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aqueous ammonia (8.0 ml) and N,N-diisopropylethylamine (13.2 ml) were dissolved into 150 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine (10.0 g) in dichloromethane (30 ml) at 0° C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. The precipitate was filtered off. The filter cake was recrystallized to obtain a yellow solid (8.1 g) in a yield of 90.1%. 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 9.02 (s, 1H), 8.60 (s, 1H) ppm.

Workup

  1. additionAfter the completion of the dropwise addition
  2. customto react for 1 hour
  3. filtrationThe precipitate was filtered off
  4. customThe filter cake was recrystallized

Sources & evidence

ORD record
ord-69558ff02a0444dab71bbcceb0f0c4dc
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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