Ammonium formate → HCID 9945392, compound

HRID 1795926Notes

Reaction equation

HRID 1795926 reaction equation
C([O:4][CH2:5][C:6]1[O:7][C:8]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]([CH2:19][C:20]3[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[N:24][CH:25]=3)[C:9]=2[CH:10]=1)C=C.C([O-])=O.[NH4+]>C(#N)C>[NH2:26][C:23]1[N:22]=[C:21]([NH2:27])[C:20]([CH2:19][C:11]2[C:9]3[CH:10]=[C:6]([CH2:5][OH:4])[O:7][C:8]=3[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 10292567HCID 10292567, compound

Product 1

HCID 9945392HCID 9945392, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under argon, to a solution of 5-(2-allyloxymethyl-6,7-dimethoxy-benzofuran-4-ylmethyl)-pyrimidine-2,4-diamine (610 mg, 1.64 mmol) in ACN was added Pd(PPh3)4 complex (571 mg, 0.424 mmol) and ammonium formate (519 mg, 8.23 mmol). The reaction mixture was stirred at reflux for 2 h. Then the reaction was quenched with 1N HCl, the impurities were extracted with ethyl acetate and the solution neutralised with Na2CO3 to pH=7 and saturated with NaOAc. The compound was extracted with ACN dried over MgSO4 and the solvent evaporated to give [4-(2,4-diamino-pyrimidin-5-ylmethyl)-6,7-dimethoxy-benzofuran-2-yl]-methanol (497 mg, 84%) as a yellow solid.

Workup

  1. temperatureat reflux for 2 h
  2. customThen the reaction was quenched with 1N HCl
  3. extractionthe impurities were extracted with ethyl acetate
  4. extractionThe compound was extracted with ACN
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-e2f3495e482d41828fcbf85a24e52fdc
Source dataset
uspto-grants-2006_04
Patent number
US07030130B2

Reaction notes

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