2-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amine → 1-(1-methyl-1H-imidazol-2-yl)-4-phenoxy-1H-pyrazolo[3,4-d]pyrimidine

HRID 1098249

Reaktionsgleichung

Reaktionsgleichung von HRID 1098249
Cl.[NH:2]([C:4]1[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=1)[NH2:3].[O:10]([C:17]1[C:22]([CH:23]=O)=[C:21](OC2C=CC=CC=2)[N:20]=[CH:19][N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C1COCC1>[CH3:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N:2]1[C:21]2=[N:20][CH:19]=[N:18][C:17]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:22]2[CH:23]=[N:3]1

Komponenten

5

Edukt 3

HCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 574386554,6-Diphenoxypyrimidine-5-carbaldehydeHCID 574386662-Hydrazinyl-1-methyl-1H-imidazole hydrochloride

Produkt 1

HCID 575045581-(1-methyl-1H-imidazol-2-yl)-4-phenoxy-1H-pyrazolo[3,4-d]pyrimidineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Hydrazinyl-1-methyl-1H-imidazole hydrochloride (Intermediate AV2) (305 mg, 2.05 mmol) was added to 4,6-diphenoxypyrimidine-5-carbaldehyde (Intermediate Z2) (600 mg, 2.05 mmol) in THF (15 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 (2.8 g, 6.2 mmol) was added and sealed into a microwave tube. The reaction was heated to 120° C. for 10 hours in the 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 0 to 5% MeOH in DCM to afford the product (190 mg, 32%). 1H NMR (400 MHz, CDCl3) δ 3.59 (3H, s), 6.95 (1H, d), 7.11 (1H, d), 7.24-7.20 (2H, m), 7.32-7.26 (1H, m), 7.44 (2H, m), 8.03 (1H, s), 8.59 (1H, s); m/z (ES+) (M+H)+=293; HPLC tR=1.65 min.

Aufarbeitung

  1. customsealed into a microwave tube
  2. temperatureThe reaction was heated to 120° C. for 10 hours in the 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 0 to 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-aed5e06cdec8432c8ea3023610339f1b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143263B2

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