2-(Trifluoromethyl)phenylhydrazine → HCID 57504514, compound

HRID 1098161

Reaction equation

HRID 1098161 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[O:13]([C:20]1[C:25]([CH:26]=O)=[C:24](OC2C=CC=CC=2)[N:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C1COCC1>[O:13]([C:20]1[N:21]=[CH:22][N:23]=[C:24]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:11])([F:12])[F:1])[N:10]=[CH:26][C:25]=12)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 574386554,6-Diphenoxypyrimidine-5-carbaldehyde

Product 1

HCID 57504514HCID 57504514, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-(trifluoromethyl)phenyl)hydrazine (CAS no. 365-34-4) (102 mg, 0.58 mmol) was added to 4,6-diphenoxypyrimidine-5-carbaldehyde (Intermediate Z2) (169 mg, 0.58 mmol) in THF (2 mL) the resulting solution was stirred at room temperature for 5 minutes. 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (526 mg, 1.16 mmol) was added and sealed into a microwave tube. The reaction was heated to 150° C. for 10 hours in a microwave reactor and cooled to RT. The reaction mixture was filtered and evaporated to dryness. The crude product was purified by flash silica chromatography, eluting with 10 to 80% ethyl acetate in isohexane to afford the product (88 mg, 42.7%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.33 (2H, m), 7.34-7.39 (1H, m), 7.49-7.58 (3H, m), 7.67-7.71 (1H, m), 7.74-7.78 (1H, m), 7.90-7.92 (1H, m), 8.08 (1H, s), 8.56 (1H, s); m/z (ES+) (M+H)+=357; HPLC tR=2.66 min.

Workup

  1. customsealed into a microwave tube
  2. temperatureThe reaction was heated to 150° C. for 10 hours in a microwave reactor
  3. temperaturecooled to RT
  4. filtrationThe reaction mixture was filtered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 10 to 80% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-e1a964ae487e4f749ff07b45aea31f7a
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Linked notes

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