Furfuryl Alcohol → HCID 22594075, compound

HRID 1760976Notes

Reaction equation

HRID 1760976 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16](=[O:30])[C:17]3[CH:22]=[C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:20]=[C:19]([F:29])[CH:18]=3)[CH:12]=[CH:11][C:10]=2[CH3:31])[CH:5]=[CH:4][N:3]=1.[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[CH2:37][OH:38].CC(C)([O-])C.[K+]>>[F:29][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=1)[C:16]([NH:15][C:13]1[CH:12]=[CH:11][C:10]([CH3:31])=[C:9]([CH:14]=1)[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:38][CH2:37][C:33]2[O:32][CH:36]=[CH:35][CH:34]=2)[N:7]=1)=[O:30]

Participants

4

Reactant 3

HCID 7361Furfuryl AlcoholHCID 22594088HCID 22594088, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22594075HCID 22594075, compoundYield 82.9%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-[5-(3-fluoro-5-morpholinobenzamido)-2-methylanilino]pyrimidine (0.18 g), approximately one equivalent of 2-furylmethanol (0.043 g) and potassium tert-butoxide (1M in tert-butanol, 0.88 ml) was stirred and heated to 100° C. for 2 hours. The mixture was partitioned between methylene chloride and water and the organic phase was washed with brine, dried over sodium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent followed by increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution. There was thus obtained the title compound as a solid (0.17 g); NMR Spectrum: (DMSOd6) 2.17 (s, 3H), 3.2 (m, 4H), 3.73 (m, 4H), 5.01 (s, 2H), 6.29 (d, 1H), 6.42 (m, 2H), 6.97 (m, 1H), 7.1 (m, 1H), 7.24 (m, 2H), 7.49 (d, 1H), 7.63 (s, 1H), 7.87 (s, 1H), 8.03 (d, 1H), 9.03 (s, 1H), 10.14 (s, 1H); Mass Spectrum: M+H+ 504.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  7. temperatureby increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution

Sources & evidence

ORD record
ord-22faa92087b74764b6934af8d256deef
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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