Morpholine → 8-Chloro-3-pentyl-1-(3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]propyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1097650

反応式

HRID 1097650 の反応式
[C:1]1([CH2:7][C:8]2[N:12]=[C:11]([CH2:13][CH2:14][CH2:15]O)[O:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[N:26](CC=C)[C:25]2[C:24](=[O:30])[NH:23][C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=2[N:19]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:18]1[NH:26][C:25]2[C:24](=[O:30])[N:23]([CH2:15][CH2:14][CH2:13][C:11]3[O:10][N:9]=[C:8]([CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:12]=3)[C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=2[N:19]=1

参加物

8

反応物 5

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneHCID 593955733-[3-(Phenylmethyl)-1,2,4-oxadiazol-5-yl]-1-propanol

生成物 1

HCID 593957888-Chloro-3-pentyl-1-(3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]propyl)-3,7-dihydro-1H-purine-2,6-dione

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]-1-propanol (88 mg, 0.4 mmol) in THF (4 ml) was treated with 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.34 mmol) and PPh3 (115 mg, 0.44 mmol) under nitrogen. DBAD (101 mg, 0.44 mmol) was added in one portion and the reaction left to react for 5 h. The mixture was degassed by applying a vacuum and then nitrogen was introduced. Pd(PPh3)4 (39 mg, 0.034 mmol) was added and the mixture degassed once more. Morpholine (294 μl, 3.4 mmol) was added and the mixture was stirred under nitrogen for 3 h. The mixture was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. The title compound was obtained as a white solid after purification by MDAP (64 mg, 42%).

後処理

  1. waitthe reaction left
  2. customto react for 5 h
  3. customThe mixture was degassed
  4. additionnitrogen was introduced
  5. customthe mixture degassed once more
  6. customThe mixture was partitioned between 2M HCl (aq) and EtOAc
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b15438e57bd24b7aaab077db1851457d
出典データセット
uspto-grants-2012_03
特許番号
US08143264B2

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