Ethyl Acetate → 4-Amino-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one

HRID 2237630

반응식

HRID 2237630 반응식
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C([N:21](CC)C(C)C)C.Cl[C:28]1[C:33]([C:34](Cl)=[O:35])=[C:32](Cl)[N:31]=[CH:30][N:29]=1.CCOC(C)=O>C1NC2NC(N)=NC(=O)C=2N2C1CN(C1C=CC(C(N[C@H](C(O)=O)CCC(O)=O)=O)=CC=1)C2.CCCCCCC>[NH2:21][C:28]1[C:33]2[C:34](=[O:35])[N:11]([C:12]3[CH:13]=[CH:14][C:15]([I:18])=[CH:16][CH:17]=3)[CH2:10][CH2:9][O:8][C:32]=2[N:31]=[CH:30][N:29]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 521913N,N-Diethyl-2-propanamineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 59302533N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-4-iodoaniline

생성물 1

HCID 593025304-Amino-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one

시약·촉매·용매 2

HCID 8900Heptane용매HCID 178508906HCID 178508906, 화합물용매

실험 절차

To a cooled (ice/water), stirred solution of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-iodoaniline (1.34 g, 2.78 mmol) and diethylisopropylamine (0.7 mL, 4.0 mmol) in MTHF (5 mL) was added 4,6-dichloroprimidine-5-carbonyl chloride (560 mg, 2.65 mmol). After 5 minutes, the cooling bath was removed and the slurry was stirred for 5 hours. Aqueous hydrochloric acid (1N, 5 mL) was added and the mixture was allowed to stand for 72 hours. The layers were separated and the aqueous layer was washed with MTHF (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo to afford an oil. Chromatography (40 g silica gel column, 20-100% EtOAc:heptane) afforded the title compound, 542 mg. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.62 (d, 2H), 7.17 (d, 2H), 4.07 (t, 2H), 3.91 (q, 2H). m/z=438.0 (M+1).

후처리

  1. customthe cooling bath was removed
  2. additionAqueous hydrochloric acid (1N, 5 mL) was added
  3. waitto stand for 72 hours
  4. customThe layers were separated
  5. washthe aqueous layer was washed with MTHF (2×)
  6. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford an oil

출처 및 근거

ORD 기록
ord-76521802846e4ca3acc1f88eb4436c47
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718645B2

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