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Carbon tetrabromide → HCID 67258656、化合物

HRID 1476632
ノート
印刷プレビュー

反応式

HRID 1476632 の反応式
[CH2:1]([O:4][CH2:5][C:6]1[N:10]=[C:9]([CH2:11]O)[O:8][N:7]=1)[CH2:2][CH3:3].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:37]=[C:38]1[NH:43][C:42]2[CH:44]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[S:46][C:41]=2[C:40](=[O:53])[N:39]1[CH:54]1[CH2:59][CH2:58][N:57]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:56][CH2:55]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CN(C=O)C>[O:37]=[C:38]1[N:43]([CH2:11][C:9]2[O:8][N:7]=[C:6]([CH2:5][O:4][CH2:1][CH2:2][CH3:3])[N:10]=2)[C:42]2[CH:44]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[S:46][C:41]=2[C:40](=[O:53])[N:39]1[CH:54]1[CH2:59][CH2:58][N:57]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:56][CH2:55]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 63758128HCID 63758128、化合物HCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

生成物 1

HCID 67258656HCID 67258656、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of [3-(propoxymethyl)-1,2,4-oxadiazol-5-yl]methanol (250 mg, compound D22) and CBr4 (620 mg) in DCM (5 ml) are added triphenylphosphine (490 mg) and the reaction mixture is stirred for 15 min at RT. This solution is added to a stirred suspension of tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (0.5 g; compound B50) and potassium carbonate (323 mg) in DMF and the reaction mixture is stirred for 3 h at 65° C. Afterwards the solvent is removed under vacuo, the resulting residue is treated with EtOAc/cyclohexane (1:1) and the suspension is filtered. The filtrate is purified by flash chromatography (silica gel, eluent EtOAc/cyclohexane 1:1) and the product fraction are washed with diethylether to give the title compound as a solid.

後処理

  1. stirringthe reaction mixture is stirred for 3 h at 65° C
  2. customAfterwards the solvent is removed under vacuo
  3. additionthe resulting residue is treated with EtOAc/cyclohexane (1:1)
  4. filtrationthe suspension is filtered
  5. customThe filtrate is purified by flash chromatography (silica gel, eluent EtOAc/cyclohexane 1:1)
  6. washthe product fraction are washed with diethylether

出典と根拠

ORDレコード
ord-98fddceeaea447e38ee9832be020f088
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018175B2

反応ノート

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