Hydrochloric Acid → HCID 57818792, compound

HRID 705592Notes

Reaction equation

HRID 705592 reaction equation
[F:1][C:2]1[C:3]([NH:18][NH2:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[N:6][CH:7]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=O.Cl>CCOCC.CCO>[F:1][C:2]1[C:3]([NH:18]/[N:19]=[CH:25]/[C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73642-ThiophenecarboxaldehydeHCID 57818915HCID 57818915, compound

Product 1

HCID 57818792HCID 57818792, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A 20 mL vial was charged with 5-fluoro-4-hydrazinyl-2-(3-methoxybenzyloxy)-pyrimidine (74.7 mg, 0.283 mmol), EtOH (2 mL), thiophene-2-carbaldehyde (26 μL, 0.284 mmol) and 1 M HCl in Et2O (14 μL, 0.014 mmol) and heated at 50° C. on shaker. After 90 minutes, the reaction was cooled to room temperature concentrated on high vacuum to provide the title compound (77.8 mg, 77%) as a yellow solid: mp 136-139° C.; 1H NMR (300 MHz, DMSO-d6) δ 11.46 (bs, 1H), 8.50 (bs, 1H), 8.16 (d, J=3.6 Hz, 1H), 7.64 (d, J=5.0 Hz, 1H), 7.41 (d, J=3.4 Hz, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.12 (dd, J=3.8, 4.8 Hz, 1H), 7.04 (m, 2H), 6.88 (dd, J=2.4, 8.3 Hz, 1H), 5.27 (s, 2H), 3.73 (s, 3H); MS (ESI) m/z 359.2 (M+H)+, 357.2 (M−H)−.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated on high vacuum

Sources & evidence

ORD record
ord-be468f3e619145d9a1556ddf7051ee16
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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