Ammonium formate → HCID 68165224, compound

HRID 921321Notes

Reaction equation

HRID 921321 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]([O:42][CH3:43])[CH:16]=2)(=[O:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd]>[CH3:43][O:42][C:17]1[CH:16]=[C:15]([P:11]2(=[O:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:20]=[CH:19][C:18]=1[NH:21][C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 68165434HCID 68165434, compound

Product 1

HCID 68165224HCID 68165224, compoundYield 42.2%

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-c939213db67e4063ae02d4253b5de14e
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

Loading…