Sodium hydride → HCID 18931068, compound

HRID 1599021Notes

Reaction equation

HRID 1599021 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([O:17][CH2:18][CH2:19][O:20][C:21]2[N:26]=[CH:25][C:24]([Br:27])=[CH:23][N:22]=2)[N:5]=[C:4]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[N:3]=1.[H-].[Na+].[S:36]1[CH:40]=[CH:39][CH:38]=[C:37]1[S:41](Cl)(=[O:43])=[O:42].[Cl-].[NH4+]>O1CCCC1>[Br:27][C:24]1[CH:23]=[N:22][C:21]([O:20][CH2:19][CH2:18][O:17][C:6]2[N:5]=[C:4]([C:28]3[N:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[N:3]=[C:2]([NH:1][S:41]([C:37]3[S:36][CH:40]=[CH:39][CH:38]=3)(=[O:43])=[O:42])[C:7]=2[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[N:26][CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 855182-Thiophenesulfonyl chlorideHCID 18931075HCID 18931075, compound

Product 1

HCID 18931068HCID 18931068, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-amino-6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine (100 mg), sodium hydride (60 dispersion, 53.5 mg) and tetrahydrofuran (3 ml) is stirred at room temperature for 20 minutes. To the mixture is added thiophenesulfonyl chloride (23.4 mg), and the mixture is stirred for 22 hours. The reaction solution is treated with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform: methanol=10:1) to give the title compound (49.1 mg).

Workup

  1. stirringthe mixture is stirred for 22 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by preparative thin layer chromatography (solvent; chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-6b476f5c5d9d4dab8dd1084355d5682f
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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