Sodium hydride → HCID 58016886, compound

HRID 1926919Notes

Reaction equation

HRID 1926919 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:30]3[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH:35]=O)=[N:28][CH:27]=[N:26][C:25]=3[O:24][C:23]=2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:18][CH:17]=1>C1COCC1.ClCCl.O>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:35]/[CH2:34][CH2:33][CH2:32][NH:31][C:29]1[C:30]2[C:22]([C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[C:23]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[O:24][C:25]=2[N:26]=[CH:27][N:28]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 58016833HCID 58016833, compound

Product 1

HCID 58016886HCID 58016886, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 0.095 ml (0.588 mmol) trimethyl phosphonoacetate dropwise at RT to a suspension of 21.6 mg sodium hydride (60% dispersion in oil, approx. 0.539 mmol) in 2 ml THF. Stir the mixture for a further 1 h and then add 190 mg (0.49 mmol) 4-{[5-(4-methoxyphenyl)-6-phenylfuro-[2,3-d]pyrimidin-4-yl]amino}butanal. Stir overnight at RT and then dilute the mixture with dichloromethane and water. Wash the organic phase with saturated sodium chloride solution, dry, and concentrate under vacuum. The target compound is isolated from the raw product by preparative RP-HPLC (twice) (gradient: water/acetonitrile). 23.4 mg (10.8% of theor.) of the desired product is obtained.

Workup

  1. stirringStir overnight at RT
  2. washWash the organic phase with saturated sodium chloride solution
  3. customdry
  4. concentrationconcentrate under vacuum
  5. customThe target compound is isolated from the raw product by preparative RP-HPLC (twice) (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-3c2622e0de2a4930b83f85716e624367
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

Loading…