Ethyl isocyanate → HCID 54337489, compound

HRID 567767Notes

Reaction equation

HRID 567767 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:24][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.CC(N(C)C)=O.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][C:15]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:34]([NH:33][CH2:31][CH3:32])=[O:35])=[CH:3][CH:4]=3)[NH:24][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 31374DimethylacetamideHCID 21262612HCID 21262612, compound

Product 1

HCID 54337489HCID 54337489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg (0.89 mmol) of 6-(4-aminophenyl)-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine (see Stage 19.5), dissolved in 20 ml of abs. THF and 2 ml (3.56 mmol) of DMA are treated with 0.29 ml of ethyl isocyanate (FLUKA) with exclusion of moisture and heated under reflux until starting material is no longer present in the TLC (24 h). The reaction mixture is evaporated to dryness in vacuo and the crude product is chromatographed on silica gel, ethyl acetate/methanol being used as the eluent. Fractions which contain the desired product are combined and evaporated to dryness. The residue is dissolved in a little THF. The target compound is precipitated/crystallized by addition of n-hexane. Colorless crystals of 4-(3-chloroanilino)-6-(4-[N3-ethylureido]phenyl)-7H-pyrrolo[2,3-d]pyrimidine are obtained; m.p.>290° C., FAB-MS: (M+H)+=407.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customin the TLC (24 h)
  4. customThe reaction mixture is evaporated to dryness in vacuo
  5. customthe crude product is chromatographed on silica gel, ethyl acetate/methanol being
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in a little THF
  8. customThe target compound is precipitated/crystallized by addition of n-hexane

Sources & evidence

ORD record
ord-f50de8deaaaf4aaea9de686ade0f1ee6
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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