Tetrahydrofuran → HCID 67053288, compound

HRID 1471980Notes

Reaction equation

HRID 1471980 reaction equation
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[C:15]([NH2:31])=[CH:14][N:13]=2)=[C:7]([O:32][CH3:33])[CH:6]=1)([CH3:4])=[O:3].C1C[O:37][CH2:36]C1>>[CH3:4][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]3[C:15]([NH:31][C:36](=[O:37])[N:18]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH:28]([CH3:29])[CH3:30])(=[O:27])=[O:26])=[CH:14][N:13]=2)=[C:7]([O:32][CH3:33])[CH:6]=1)([CH3:1])=[O:3]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 68165223HCID 68165223, compound

Product 1

HCID 67053288HCID 67053288, compound

Procedure

To a solution of N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4,5-triamine (as prepared in Example 28: 40 mg, 0.082 mmol) in THF was added N,N′-Carbonyldiimidazole (40 mg, 0.25 mmol). The solution was stirred at room temperature overnight. The solution was concentrated under reduced pressure and diluted with water and extracted with Ethyl Acetate. The combined organic layer was washed with brine and dried over Magnesium Sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by RP Prep-HPLC to obtain the desired product as an off white solid. MS/ES+: m/z=516

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with Ethyl Acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Magnesium Sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by RP Prep-HPLC

Sources & evidence

ORD record
ord-ea553834d9364e60a10d7f94b7ea5cb3
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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