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Carbon tetrabromide → HCID 67258656, 화합물

HRID 1476632
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HRID 1476632 반응식
[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
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참가 물질

8

반응물 5

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

생성물 1

HCID 67258656HCID 67258656, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98fddceeaea447e38ee9832be020f088
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018175B2

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