Iodine chloride → 2-Amino-6-ethylamino-4-iodopyrimidine hydrochloride

HRID 1666256Notes

Reaction equation

HRID 1666256 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[C:4]([NH:8][CH2:9][CH3:10])[N:3]=1.[I:11][Cl:12]>CO>[ClH:12].[NH2:1][C:2]1[N:7]=[C:6]([I:11])[CH:5]=[C:4]([NH:8][CH2:9][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 544617992-Amino-6-ethylaminopyrimidine

Product 1

HCID 866284152-Amino-6-ethylamino-4-iodopyrimidine hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-6-ethylaminopyrimidine (98 g, 0.64 mol) in methanol (1.6 L) was added ICl (115.0 g, 0.71 mol) in a small portion at 15° C. Then the reaction mixture was stirred at room temperature for 3 h (monitored by LC/MS). After evaporation of solvent by rotary evaporator, the residue was triturated with acetone. 2-amino-6-ethylamino-4-iodopyrimidine hydrochloride (188.5 g, 93% isolated yield) was obtained by vacuum filtration and drying. 1H NMR (400 MHz, CD3OD) δ 3.58 (q, 2H), 2.14 (s, 3H), 1.11 (t, 3H); MS (EI) for C7H11N4ClI: 279.1 (MH+).

Workup

  1. customAfter evaporation of solvent
  2. customby rotary evaporator
  3. customthe residue was triturated with acetone

Sources & evidence

ORD record
ord-c65c7f92b84447e393e1843d72b121e1
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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