Ethanol → HCID 57818915, compound

HRID 705591Notes

Reaction equation

HRID 705591 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:3]=1.CCO.O.[NH2:23][NH2:24]>O>[F:8][C:7]1[C:2]([NH:23][NH2:24])=[N:3][C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 57818820HCID 57818820, compound

Product 1

HCID 57818915HCID 57818915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 125 mL Erlenmeyer flask was charged with 4-chloro-5-fluoro-2-(3-methoxybenzyl-oxy)pyrimidine (1.50 g, 5.58 mmol) and EtOH (50 mL). Hydrazine monohydrate (900 μL, 18.5 mmol) was added, and the resulting mixture was allowed to stir at room temperature. After 22 h, the reaction was transferred to a 500 mL Erlenmeyer flask and diluted with water (200 mL), whereupon a white solid began to precipitate from solution. After stirring for 7 h, solid product was collected in a fritted funnel and rinsed with excess water. After drying on the frit, the title compound was obtained (1.23 g, 83%) as a white solid: mp 103-106° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.92 (bs, 1H), 7.86 (d, J=3.6 Hz, 1H), 7.27 (t, J=8.1 Hz, 1H), 6.94-7.01 (m, 2H), 6.87 (dd, J=2.4, 7.9 Hz, 1H), 5.24 (s, 2H), 4.46 (bs, 2H), 3.74 (s, 3H); MS (ESI) m/z 265.2 (M+H)+, 263.2 (M−H)−.

Workup

  1. customto precipitate from solution
  2. stirringAfter stirring for 7 h
  3. customsolid product was collected in a fritted funnel
  4. washrinsed with excess water
  5. customAfter drying on the frit

Sources & evidence

ORD record
ord-fda2fc04b2fb40b48212cf70dcb1d785
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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