Morpholine → HCID 69309555, compound

HRID 2375270Notes

Reaction equation

HRID 2375270 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:4][N:3]1[S:5]([C:8]1[CH:27]=[CH:26][C:11]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[N:23]([CH3:24])[C:22]([CH3:25])=[N:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[O:32]1[CH2:33][CH2:34][N:29]([CH2:4][C:2]([NH:3][S:5]([C:8]2[CH:27]=[CH:26][C:11]([NH:12][C:13]3[N:18]=[C:17]([C:19]4[N:23]([CH3:24])[C:22]([CH3:25])=[N:21][CH:20]=4)[CH:16]=[CH:15][N:14]=3)=[CH:10][CH:9]=2)(=[O:7])=[O:6])([CH3:1])[CH3:28])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86598686HCID 86598686, compound

Product 1

HCID 69309555HCID 69309555, compoundYield 82%

Procedure

2-[4-(2,2-Dimethylaziridin-1-ylsulphonyl)anilino]-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Example 47; 200 mg, 0.502 mmol) was dissolved on warming in morpholine (4.7 ml, excess) and stirred at room temperature for 3 days. The excess morpholine was removed in vacuo and the residue dissolved in EtOAc (40 ml) and washed with water (3×40 ml), dried the solvent evaporated in vacuo. The crude product was triturated with ether filtered washed with ether and air-dried to give the title compound (200 mg, 82%) as a white solid. NMR 1.03 (s, 6H), 2.27 (s, 2H), 2.38 (s, 3H), 2.47 (m, 4H), 3.52 (m, 4H), 3.95 (s, 3H), 7.05 (s, 1H), 7.2 (d, 1H), 7.63 (s, 1H), 7.72 (d, 2H), 7.88 (d, 2H), 8.43 (d, 1H), 9.86 (s, 1H); m/z 486.

Workup

  1. customThe excess morpholine was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (40 ml)
  3. washwashed with water (3×40 ml)
  4. customdried the solvent
  5. customevaporated in vacuo
  6. customThe crude product was triturated with ether
  7. filtrationfiltered
  8. washwashed with ether
  9. customair-dried

Sources & evidence

ORD record
ord-6b134cbfaf474b18b01c971d845f7e17
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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