Ammonium Hydroxide → 4-Pyrimidinamine, 6-chloro-5-nitro-

HRID 528010Notes

Reaction equation

HRID 528010 reaction equation
[OH-].[NH4+:2].[Cl:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8](Cl)[N:7]=[CH:6][N:5]=1>C(OCC)C.CO>[Cl:3][C:4]1[N:5]=[CH:6][N:7]=[C:8]([NH2:2])[C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 203124,6-Dichloro-5-nitropyrimidine

Product 1

HCID 1012294-Pyrimidinamine, 6-chloro-5-nitro-Yield 74.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5-nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3ClN4O2: 175 (MH+).

Workup

  1. additionThe addition
  2. additionUpon completion of addition
  3. filtrationthe resulting yellow solid was filtered off
  4. washwashed with water and hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-afc9db131f1c4cbfad289bbe6f81e6f2
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

Loading…