Sodium Hydroxide → 6-Chloro-5-iodopyrimidin-4-amine

HRID 2036577Notes

Reaction equation

HRID 2036577 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.FC(F)(F)S(O)(=O)=O.[I:17]N1C(=O)CCC1=O.[OH-].[Na+]>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:17]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 468558336-Chloro-5-iodopyrimidin-4-amine

Procedure

To a suspension of 6-chloropyrimidin-4-amine (5.29 g, 40.8 mmol) and trifluoro-methane sulfonic acid (40 mL, 452 mmol) was added N-iodosuccinimide (9.19 g, 40.8 mmol). The mixture was stirred for 3 h at rt. The mixture was poured into 50 mL of ice containing 15 g of NaOH with stirring for 10 min. The resulting precipitate was filtered washed with water, triturated in DCM and collected by filtration to give 6-chloro-5-iodopyrimidin-4-amine: 1H NMR (400 MHz, DMSO-d6) δ 8.11 (s, 1H); LC-MS (ESI) m/z 255.9 [M+H]+.

Workup

  1. stirringwith stirring for 10 min
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customtriturated in DCM
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-52dccfc1f2fc4ddca5934e41cdadfd50
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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