Formaldehyde → HCID 57677697, compound

HRID 492915Notes

Reaction equation

HRID 492915 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][CH3:20])=[O:15])[CH:8]=2)=[C:4]([F:23])[CH:3]=1.[CH2:24]=O>O1CCCC1>[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:17][CH2:18][N:19]([CH3:24])[CH2:20]3)=[O:15])[CH:8]=2)=[C:4]([F:23])[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 23153191HCID 23153191, compound

Product 1

HCID 57677697HCID 57677697, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To 1-[6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]-3-(2-methylaminoethyl)urea (56.8 mg) dissolved in tetrahydrofuran (5 ml) was added paraformaldehyde (59 mg), followed by stirring at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, and partitioned between ethyl acetate and 2N aqueous solution of sodium hydroxide. The separated organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=95:5) to provide the titled compound (22.4 mg, 38%) as white powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and 2N aqueous solution of sodium hydroxide
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a residue, which
  7. customwas purified by silica gel column chromatography (Fuji Silysia NH, eluent

Sources & evidence

ORD record
ord-713d1b4c3c5a49649b438ffd10ceeed1
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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