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

HRID 2171519Notes

Reaction equation

HRID 2171519 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[I-].[K+].Cl[CH2:17][C:18]1[N:19]=[C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])[N:23]=[C:22]([S:34][CH2:35][CH3:36])[N:21]2[CH:37]=1>CN(C=O)C>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[C:24]1[N:23]=[C:22]([S:34][CH2:35][CH3:36])[N:21]2[CH:37]=[C:18]([CH2:17][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:19]=[C:20]2[CH:25]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 8471TriethylamineHCID 593129982-(Chloromethyl)-7-(2,4-dichlorophenyl)-5-(ethylsulphanyl)imidazo[1,2-c]pyrimidine

Product 1

HCID 593130757-(2,4-Dichlorophenyl)-5-(ethylsulphanyl)-2-(morpholin-4-ylmethyl)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

102 mg (1.17 mmol) of morpholine are introduced into 7 ml of DMF at 0° C., and 236 mg (0.78 mmol) of triethylamine and a catalytic amount of potassium iodide are added. A solution of 290 mg of 2-(chloromethyl)-7-(2,4-dichlorophenyl)-5-(ethylsulphanyl)imidazo[1,2-c]pyrimidine (Example 91A) 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 214 mg (43% 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 214 mg (43% of theory) of product

Sources & evidence

ORD record
ord-4f700a0d7dc84dbb9bec7dcf1a301372
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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