Thiomorpholine → 5-Fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-N4-[2-(4-thiomorpholinylcarbonyl)phenyl]-2,4-pyrimidinediamine

HRID 1362879Notes

Reaction equation

HRID 1362879 reaction equation
[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26](OCC)=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:10]=2)=[N:6][CH:7]=1.[NH:35]1[CH2:40][CH2:39][S:38][CH2:37][CH2:36]1>>[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([N:35]2[CH2:40][CH2:39][S:38][CH2:37][CH2:36]2)=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 67164ThiomorpholineHCID 66941025Ethyl 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}benzoate

Product 1

HCID 579741995-Fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-N4-[2-(4-thiomorpholinylcarbonyl)phenyl]-2,4-pyrimidinediamine

Procedure

Ethyl 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}benzoate (200 mg, 0.51 mmoles) and thiomorpholine (2 mL) were heated at 120° C. for 48 h. The reaction mixture was concentrated to dryness under vacuum and the title compound was purified by flash chromatography on silica gel (using ethyl acetate containing 0.1% triethylamine). MS: M(C27H31FN6O2S)=522.2, (M+H)+=523.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under vacuum
  2. customthe title compound was purified by flash chromatography on silica gel (using ethyl acetate containing 0.1% triethylamine)

Sources & evidence

ORD record
ord-31faa3cc7bd34dfa8bdd8eaa269e6086
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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