Cesium carbonate → HCID 18507422, compound

HRID 1355994Notes

Reaction equation

HRID 1355994 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:15])[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([O:15][CH2:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 136401064HCID 136401064, compound

Product 1

HCID 18507422HCID 18507422, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 400 mg (1.98 mmol) 2-amino-4-furan-2-yl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile in 15 ml DMF were added 1.93 g (5.94 mmol) cesium carbonate and 847 mg (3.96 mmol) 2-(chloromethyl)quinoline hydrochloride and stirring continued for 16 h ours at 100° C. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether/methanol to afford 110 mg (16%) 2-amino-4-furan-2-yl-6-(quinolin-2-ylmethoxy)-pyrimidine-5-carbonitrile as an orange crystalline solid. ES-MS m/e (%): 344 (M+H+, 100).

Workup

  1. customat 100° C
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in ether/methanol

Sources & evidence

ORD record
ord-c46b4d441a5f419a9deba590e3e67a28
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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