Dimethylformamide → {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid tert-butyl ester

HRID 472761Notes

Reaction equation

HRID 472761 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[NH:10][C:9]1=[O:19])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]([NH:25][C:26]1[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:27]=1[O:35][CH3:36])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>O>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N:10]([CH2:22][C:23](=[O:24])[NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:27]=2[O:35][CH3:36])[C:9]1=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 636790772-Bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamideHCID 68591435(2,4-Dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-acetic acid t-butyl ester

Product 1

HCID 68589926{1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 25 ml round bottomed flask charged with (2,4-Dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-acetic acid t-butyl ester (14.9 mg, 0.054 mmol), 2-Bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide (26.5 mg, 0.06 mmol), and Cs2CO3 (50.9 mg, 0.11 mmol) is treated with DMF (3 ml) and the solution stirred at RT. After 2 hours, the reaction mixture is treated with water and stirred for 10 minutes. The product is extracted into EtOAc and washed with water (3×10 ml). The organic portions are dried (MgSO4), filtered and concentrated to give the title compound, [M+H]+ 505

Workup

  1. stirringstirred for 10 minutes
  2. extractionThe product is extracted into EtOAc
  3. washwashed with water (3×10 ml)
  4. dry with materialThe organic portions are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-679ccb438ee04c17bdbf385ec4866b42
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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