Octanoyl chloride → HCID 20246378, compound

HRID 1589546Notes

Reaction equation

HRID 1589546 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]=1.[C:12](Cl)(=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>N1C=CC=CC=1>[C:12]([NH:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]=1)(=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8124Octanoyl chlorideHCID 219043482-Amino-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 20246378HCID 20246378, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

2-Aminopyrrolo(2,3-d)pyrimidin-4-one (6.0 g) is suspendeed in pyridine (80 ml) and, with stirring on an ice bath, n-octanoyl chloride (22.8 g) is added. The reaction mixture is warmed at 85° C. for 30 minutes and the solvent is distilled off under reduced pressure. Dilute hydrochloric acid is added to the residue and the mixture is extracted with chloroform. The extracts are combined and concentrated to dryness. The residue is dissolved in 8% (W/V) alcoholic ammonia (50 ml) and the solution is allowed to stand at room temperature to give the above-identified compound (8.9 g) as crystals.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. additionDilute hydrochloric acid is added to the residue
  3. extractionthe mixture is extracted with chloroform
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue is dissolved in 8% (W/V) alcoholic ammonia (50 ml)
  6. customto stand at room temperature

Sources & evidence

ORD record
ord-1378c903e2834285ad1631d1f6cadfcc
Source dataset
uspto-grants-1986_02
Patent number
US04571423

Reaction notes

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