Potassium Iodide → 7-Chloro-5-(methylthio)-2-(morpholin-4-ylmethyl)imidazo[1,2-c]pyrimidine

HRID 2171489Notes

Reaction equation

HRID 2171489 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[I-].[K+].[Cl:16][C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]2[CH:25]=[C:26]([CH2:28]Cl)[N:27]=[C:19]2[CH:18]=1>CN(C=O)C>[Cl:16][C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]2[CH:25]=[C:26]([CH2:28][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:27]=[C:19]2[CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 8471TriethylamineHCID 592992327-Chloro-2-(chloromethyl)-5-methylsulfanyl-imidazo[1,2-c]pyrimidine

Product 1

HCID 593129667-Chloro-5-(methylthio)-2-(morpholin-4-ylmethyl)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

158 mg (1.81 mmol) of morpholine are introduced into 10 ml of DMF at 0° C., and 367 mg (3.63 mmol) of triethylamine and a catalytic amount of potassium iodide are added. A solution of 300 mg of 7-chloro-2-(chloromethyl)-5-(methylthio)imidazo[1,2-c]pyrimidine (Example 26A) in DMF is then slowly added dropwise. The mixture is allowed to reach RT and is stirred at this temperature for a further 16 h. Purification of the crude product by preparative HPLC and drying under high vacuum result in 221.8 mg (41% of theory) of product.

Workup

  1. customto reach RT
  2. customPurification of the crude product by preparative HPLC
  3. customdrying under high vacuum
  4. customresult in 221.8 mg (41% of theory) of product

Sources & evidence

ORD record
ord-b5b1ad34339d4f8890508d802aee3c4e
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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