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 1098249노트

반응식

HRID 1098249 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aed5e06cdec8432c8ea3023610339f1b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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