HCID 136247107, compound → HCID 136247222, compound

HRID 1022451Notes

Reaction equation

HRID 1022451 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:23])[CH2:11][N:10]([C:12]3[NH:13][C:14](=[O:22])[C:15]4[CH:20]=[CH:19][N:18]([CH3:21])[C:16]=4[N:17]=3)[CH2:9]2)=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:21][N:18]1[C:16]2[N:17]=[C:12]([N:10]3[CH2:9][C:8]([CH3:23])([C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=4)[CH2:11]3)[NH:13][C:14](=[O:22])[C:15]=2[CH:20]=[CH:19]1

Participants

6

Reactant 2

HCID 136247107HCID 136247107, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136247222HCID 136247222, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-(4-bromophenyl)-3-methylazetidin-1-yl)-7-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (100.3 mg, 269 μmol) in ethyl acetate (2.7 mL) and methanol (2.8 mL) was treated with 10% palladium on carbon (9.2 mg, ˜10% weight of starting material used). The flask was capped with a rubber septum and a hydrogen balloon was attached. The reaction was stirred at room temperature overnight. At this time, the reaction was concentrated in vacuo onto Celite®. Flash chromatography (24 g silica gel column, 20-100% ethyl acetate/hexanes) afforded 7-methyl-2-(3-methyl-3-phenyl-azetidin-1-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as an off-white solid (43.2 mg, 54.6%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.61 (s, 3H) 3.53 (s, 3H) 4.10 (d, J=8.67 Hz, 2H) 4.24 (d, J=8.29 Hz, 2H) 6.23 (d, J=3.01 Hz, 1H) 6.73 (d, J=3.20 Hz, 1H) 7.13-7.50 (m, 5H) 10.90 (s, 1H). LC-MS calcd. for C17H19N4O [(M+H)+] 295, obsd. 295.1.

Workup

  1. customThe flask was capped with a rubber septum
  2. concentrationAt this time, the reaction was concentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-ab92ac9baa8345a5bb35d1a22759a88d
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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