Triethylamine → HCID 59160587, compound

HRID 1500051Notes

Reaction equation

HRID 1500051 reaction equation
[CH2:1]([O:4][C:5]1[N:10]=[C:9](Cl)[C:8]([F:12])=[CH:7][N:6]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.O.[NH2:21][NH2:22].[CH3:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>C(O)C>[CH2:1]([O:4][C:5]1[N:10]=[C:9]([NH:21][NH:22][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([CH3:23])[CH:25]=2)[C:8]([F:12])=[CH:7][N:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 743753-Methylbenzoyl chlorideHCID 59160675HCID 59160675, compound

Product 1

HCID 59160587HCID 59160587, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 25 mL vial was charged with 2-(allyloxy)-4-chloro-5-fluoropyrimidine (72.5% pure, 175 mg, 0.673 mmol), ethanol (4 mL), triethylamine (234 μL, 1.68 mmol), and hydrazine monohydrate (34 μL, 0.706 mmol). The resulting solution was then agitated on an orbital shaker at room temperature for 90 min. 3-Methylbenzoyl chloride (93 μL, 0.706 mmol) was then added, and the reaction was further agitated for 16 h. The crude reaction mixture was concentrated under reduced pressure, and then purified by flash column chromatography (EtOAc/hexane gradient) to afford the title compound (95.8 mg, 47%) as a pale yellow solid: mp 181-185° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.44 (bs, 1H), 9.75 (bs, 1H), 8.10 (d, J=3.5 Hz, 1H), 7.65-7.75 (m, 2H), 7.37-7.43 (m, 2H), 5.95 (m, 1H). 5.25 (m, 1H), 5.15 (m, 1H), 4.63 (m, 2H), 2.37 (s, 3H); MS (ESI) m/z 303 (M+H)+, 301 (M−H)−.

Workup

  1. stirringthe reaction was further agitated for 16 h
  2. customThe crude reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. custompurified by flash column chromatography (EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-e6cd1418869945d29f449c057b2a2474
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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