Sodium hydride → HCID 18931099, compound

HRID 1599022Notes

Reaction equation

HRID 1599022 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]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]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]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]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 18931080HCID 18931080, compound

Product 1

HCID 18931099HCID 18931099, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-amino-6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(2-methoxyphenoxy)-2-morpholinopyrimidine (200 mg), sodium hydride (60% dispersion, 46.2 mg) and tetrahydrofuran (6 ml) is stirred at room temperature for 20 minutes. To the mixture is added 2-thiophenesulfonyl chloride (211 mg), and the mixture is stirred for 20 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 recrystallized from ether-hexane to give the title compound (46 mg).

Workup

  1. stirringthe mixture is stirred for 20 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 recrystallized from ether-hexane

Sources & evidence

ORD record
ord-179e902622324674b29f95ea45b24ace
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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