HCID 53637375, compound → HCID 23505741, compound

HRID 1884351Notes

Reaction equation

HRID 1884351 reaction equation
[CH2:1]([C:3]([C:7]1[C:8]2[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)=[CH:4][CH2:5][CH3:6])[CH3:2].C(C(C1C2C(C)=C(C)N(C3C(C)=CC(C)=CC=3C)C=2N=C(C)N=1)=CC)CC>C(OCC)(=O)C.[Pd]>[CH2:1]([CH:3]([C:7]1[C:8]2[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)[CH2:4][CH2:5][CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 53637375HCID 53637375, compoundHCID 54366773HCID 54366773, compound

Product 1

HCID 23505741HCID 23505741, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of two isomers, 4-(1-ethyl-butenyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine and 4-(1-n-propyl-propenyl)-2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine (67 mg, 0.185 mmol) in ethyl acetate (18 ml) and 10% Pd/C (38 mg) was hydrogenated at 50 psi for 15 hours. The mixture was filtered through Celite, a trademark for a commercially available diatomaceous earth filtering material. The filtrate was washed with brine, dried and concentrated to give 119 mg of oil. The oil was purified through silica gel column chromatography using 7% ethyl acetate in hexane as eluent to give 31 mg (46%) of the title compound as off-white crystals, mp 100-102° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. filtrationa trademark for a commercially available diatomaceous earth filtering material
  3. washThe filtrate was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3f489ff6ace4279b8c3ccecd300ab1d
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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