Formaldehyde → HCID 69355450, compound

HRID 1371486Notes

Reaction equation

HRID 1371486 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]5[O:28][CH2:29][O:30][C:23]=45)=[N:16][CH:17]=[N:18]3)=[CH:13][C:12]=2[O:31][CH3:32])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:33]=O.[OH-].[Na+]>C(O)=O>[OH:1][C:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]5[O:28][CH2:29][O:30][C:23]=45)=[N:16][CH:17]=[N:18]3)=[CH:13][C:12]=2[O:31][CH3:32])[CH2:7][CH2:6][N:5]([CH3:33])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 21936011HCID 21936011, compound

Product 1

HCID 69355450HCID 69355450, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-[2-(4-hydroxypiperidin-4-yl)ethoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline (0.065 g), formaldehyde (40% aqueous solution; 0.2 ml) and formic acid (2 ml) was stirred and heated to 100° C. for 1.5 hours. The mixture was basified to pH9.5 by the addition of 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using an 80:17:3 mixture of methylene chloride, methanol and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.021 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.8 (m, 4H), 2.05 (m, 2H), 2.8 (s, 3H), 3.15 (m, 2H), 3.3 (m, 2H), 4 (s, 3H), 4.35 (m, 2H), 6.05 (s, 2H), 6.95 (m, 3H), 7.4 (s, 1H), 8.1 (s, 1H), 8.85 (s, 1H); Mass Spectrum: M+H+ 453.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. additionan 80:17:3 mixture of methylene chloride, methanol

Sources & evidence

ORD record
ord-89fea6b08bde4e03a135ca6e0509307b
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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