Tributylphosphine → 7H-Pyrrolo[2,3-d]pyrimidine, 2,4-dichloro-7-[(tetrahydro-3-furanyl)methyl]-
Reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6]O)[CH2:2]1.C(P(CCCC)CCCC)CCC.[Cl:21][C:22]1[N:23]=[C:24]([Cl:31])[C:25]2[CH:30]=[CH:29][NH:28][C:26]=2[N:27]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C(Cl)Cl>[Cl:21][C:22]1[N:23]=[C:24]([Cl:31])[C:25]2[CH:30]=[CH:29][N:28]([CH2:6][CH:3]3[CH2:4][CH2:5][O:1][CH2:2]3)[C:26]=2[N:27]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Tetrahydrofuran-3-ylmethanol (8 mL) and tributylphosphine (22 mL) were added to a suspension of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (10 g) in CH2Cl2 (150 mL) at room temperature. 1,1′-(azodicarbonyl)dipiperidine (22 g) was added thereto under ice-cooling, and the mixture was stirred at room temperature overnight. After Hex (300 mL) was added to the reaction mixture, the mixture was stirred, and the insoluble material was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Hex:EtOAc=9:1 to 6:4), whereby 2,4-dichloro-7-(tetrahydrofuran-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (5.9 g) was obtained as a dark brown oil.
Workup
- temperatureunder ice-cooling
- additionAfter Hex (300 mL) was added to the reaction mixture
- stirringthe mixture was stirred
- customthe insoluble material was separated by filtration
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (Hex:EtOAc=9:1 to 6:4)
Sources & evidence
- ORD record
- ord-b8c8c6299d5b4a5395b3cc4f22385f13
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328118B2
Reaction notes
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