1-Bromo-2-butanone → 4-(3-chloroanilino)-6-(4-ethylthiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 567761Notes

Reaction equation

HRID 567761 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15](=[S:17])[NH2:16])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.Br[CH2:22][C:23](=O)[CH2:24][CH3:25]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[S:17][CH:22]=[C:23]([CH2:24][CH3:25])[N:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 212626564-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 1357028364-(3-chloroanilino)-6-(4-ethylthiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

57.5 mg (0.19 mmol) of 4-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine (see Example 10) and 34 ml of 1-bromo-2-butanone (Aldrich; Milwaukee/USA) in 3 ml of dioxane are heated to boiling for 2 h. Cooling, filtering the suspension and washing with isopropanol/diethyl ether yields 4-(3-chloroanilino)-6-(4-ethylthiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=13.6; FAB-MS: (M+H)+=356.

Workup

  1. temperatureCooling
  2. filtrationfiltering the suspension
  3. washwashing with isopropanol/diethyl ether

Sources & evidence

ORD record
ord-ddc511c7733c4bcd91fecbe584342563
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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