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

反応式

HRID 1098249 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aed5e06cdec8432c8ea3023610339f1b
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

関連ノート

読み込み中…