Formaldehyde → HCID 57818814, compound

HRID 705569Notes

Reaction equation

HRID 705569 reaction equation
[F:1][C:2]1[C:3]([NH2:17])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[CH2:18]=[O:19]>O1CCOCC1>[F:1][C:2]1[C:3]([NH:17][CH2:18][OH:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 50991248HCID 50991248, compound

Product 1

HCID 57818814HCID 57818814, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-fluoro-2-(4-methylbenzyloxy)pyrimidin-4-ylamine (0.10 g, 0.43 mmol) in dioxane (2 mL) was added paraformaldehyde (0.060 g, 2 mmol) and the mixture was agitated on an orbital shaker at 90° C. for 16 h, cooled, and evaporated to dryness. Purification by reverse phase chromatography afforded 0.070 g (63%) of the title compound as a white solid: mp 97-98° C.; 1H NMR (CDCl3) δ 7.94 (d, J=2.5 Hz, 1H), 7.36 (d, J=7.9 Hz, 2H), 7.19 (d, J=7.9 Hz, 2H), 5.97 (bs, 1H), 5.33 (s, 2H), 5.04-4.99 (m, 2H), 3.39 (t, J=8.0 Hz, 1H), 2.37 (s, 3H); MS (ESI) m/z 264 (M+H)+.

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-774a4548ee884e498ef7783d6427ddda
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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