Dichloromethane → HCID 58016959, compound

HRID 1926924Notes

Reaction equation

HRID 1926924 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:10][C:6]=2[N:7]=[CH:8][N:9]=1.[CH2:27]([O:29][C:30](=[O:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[CH3:28].ClCCl>C1COCC1.CN(C=O)C.O>[CH2:27]([O:29][C:30](=[O:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:4]1[C:5]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:10][C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:28]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 357781Ethyl 6-hydroxyhexanoateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 58016959HCID 58016959, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 42.8 mg sodium hydride (60% dispersion in oil, approx. 1.07 mmol) in portions, at RT, to a mixture of 300 mg (0.89 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 214 mg (1.34 mmol) 6-hydroxyhexanoic acid ethyl ester in 1.0 ml THF and 0.7 ml DMF. Stir the mixture for 1 h at RT, and then add dichloromethane and water. Wash the organic phase with saturated sodium chloride solution, dry over sodium sulphate and concentrate by vacuum evaporation. After preparative RP-HPLC, 120.9 mg (29.5% of theor.) of the target compound is isolated from the residue.

Workup

  1. washWash the organic phase with saturated sodium chloride solution
  2. dry with materialdry over sodium sulphate
  3. concentrationconcentrate by vacuum evaporation
  4. customAfter preparative RP-HPLC, 120.9 mg (29.5% of theor.) of the target compound is isolated from the residue

Sources & evidence

ORD record
ord-1cd281419b2c48c2aab3d234cb4c8a63
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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