Ammonia → 2,6-Dichloro-5-nitropyrimidin-4-amine

HRID 469183

Reaction equation

HRID 469183 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:12])[N:3]=1.CC[N:15](CC)CC.N>C1COCC1>[NH2:15][C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:12])[C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 42978432,4,6-Trichloro-5-nitropyrimidine

Product 1

HCID 3508112,6-Dichloro-5-nitropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,4,6-trichloro-5-nitropyrimidine (94 mg, 0.413 mmol) in THF (5 mL) was cooled to −78° C. and treated with Et3N (110 μL, 0.757 mmol), followed by NH3 (7 N in MeOH, 50 μL, 0.344 mmol). The reaction was warmed to 0° C. Once TLC indicated complete consumption of the starting material, the crude product solution was immediately used in the reaction below (Scheme 40).

Workup

  1. customconsumption of the starting material
  2. customthe crude product solution was immediately used in the reaction below (Scheme 40)

Sources & evidence

ORD record
ord-78d78ece27574972ab7b607ff3724d01
Source dataset
uspto-grants-2014_01
Patent number
US08629142B2

Linked notes

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