Ammonium formate → HCID 86668792, compound

HRID 1471985Notes

Reaction equation

HRID 1471985 reaction equation
C([N:8]1[CH2:13][CH2:12][P:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[C:25](Cl)=[CH:24][N:23]=3)=[C:17](OC)[CH:16]=2)(=[O:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH:44]([O-])=[O:45].[NH4+]>[Pd]>[CH3:44][O:45][C:15]1([P:11]2(=[O:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:16]=[CH:17][C:18]([NH:21][C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[CH:25]=[CH:24][N:23]=2)=[CH:19][CH2:20]1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 68165434HCID 68165434, compound

Product 1

HCID 86668792HCID 86668792, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask was charged with N2-[4-(1-benzyl-4-oxido-1,4-azaphosphinan-4-yl)-2-methoxyphenyl]-5-chloro-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine (40.0 mg, 0.0625 mmol) and 10% Pd—C (40.0 mg). The flask was evacuated and filled with nitrogen. Anhydrous methanol (2 mL) was added to the flask and the flask was equipped with a reflux condenser with a nitrogen inlet. Ammonium formate (31.5 mg, 0.500 mmol) was added in one portion at room temperature. The resulting mixture was stirred at reflux for 3 h. The reaction was filtered through a Celite pad and the Celite was washed with 2×5 mL methanol. The combined filtrate and washing was evaporated in vacuo. The crude residue was purified by prep-HPLC to afford the final compound (13.6 mg, 42% yield). MS/ES+: m/z=516.

Workup

  1. customThe flask was evacuated
  2. additionfilled with nitrogen
  3. additionAnhydrous methanol (2 mL) was added to the flask
  4. customthe flask was equipped with a reflux condenser with a nitrogen inlet
  5. temperatureat reflux for 3 h
  6. filtrationThe reaction was filtered through a Celite pad
  7. washthe Celite was washed with 2×5 mL methanol
  8. washThe combined filtrate and washing
  9. customwas evaporated in vacuo
  10. customThe crude residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-eb3705b563aa444da3dbcf435f2decd3
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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