Cesium fluoride → HCID 67285760, compound

HRID 1036593Notes

Reaction equation

HRID 1036593 reaction equation
[F-].[Cs+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH3:27])[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=3)=[C:18](I)[C:12]=2[C:11]1=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4].[N+:29]([C:32]1[CH:33]=[C:34]([CH:49]=[CH:50][CH:51]=1)[CH2:35][Sn](CCCC)(CCCC)CCCC)([O-:31])=[O:30]>CN(C=O)C.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu]I>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH3:27])[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=3)=[C:18]([CH2:35][C:34]3[CH:49]=[CH:50][CH:51]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=3)[C:12]=2[C:11]1=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 131736073-Nitro-benzyl tributyl stannaneHCID 672843262-(2-Amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 67285760HCID 67285760, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cesium fluoride (0.048 g, 0.320 mmol), palladium tetrakis(triphenylphosphine) (0.018 g, 0.016 mmol) and CuI (0.0060 g, 0.032 mmol) were added to a solution of 2-(2-amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared as described in Example 1) (0.075 g, 0.160 mmol) and 3-nitro-benzyl tributyl stannane (0.102 g, 0.240 mmol) in dry DMF (1.5 ml) under an argon atmosphere. The reaction mixture was stirred at 120° C. under microwave irradiation for 1 h. The reaction mixture was diluted with purite water (2.0 ml) and the precipitate was filtered, dissolved into DCM and purified on silica gel (DCM/MeOH from 100:0 up to 85:15), affording 2-(2-Amino-pyrimidin-4-yl)-1-methyl-3-(3-nitro-benzyl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.0558 g, 0.116 mmol, 73%).

Workup

  1. filtrationthe precipitate was filtered
  2. dissolutiondissolved into DCM
  3. custompurified on silica gel (DCM/MeOH from 100:0 up to 85:15)

Sources & evidence

ORD record
ord-ef9efe0e05fa43639d5c062ba9735aef
Source dataset
uspto-grants-2013_10
Patent number
US08546413B2

Reaction notes

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