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Bromotrimethylsilane → 2-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598118
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HRID 598118 반응식
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][CH:10]=O.Br[Si](C)(C)C.[NH2:18][C:19]1[N:24]=[C:23]([OH:25])[CH:22]=[C:21]([NH:26][CH3:27])[N:20]=1>O.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.C(#N)C>[NH2:18][C:19]1[NH:24][C:23](=[O:25])[C:22]2[C:9]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:12])=[CH:10][N:26]([CH3:27])[C:21]=2[N:20]=1
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참가 물질

8

반응물 3

HCID 76113BromotrimethylsilaneHCID 3003822-(2,4,6-Trimethylphenyl)acetaldehydeHCID 178482274HCID 178482274, 화합물

생성물 1

HCID 1364007122-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one수율 68%

시약·촉매·용매 4

HCID 11430Potassium Carbonate촉매
HCID 679
Dimethyl Sulfoxide
용매
2회
HCID 962Water용매2회
HCID 6342Acetonitrile용매2회

실험 절차

A solution of dimethylsulfoxide (468 mg, 6.00 mmol) and acetonitrile (8 ml) was added to a mixture of mesitylacetoaldehyde (904 mg, 5.57 mmol), bromotrimethylsilane (919 mg, 6.00 mmol) and acetonitrile (8 ml) at 0° C. After stirring at room temperature for 0.5 hour, the mixture was diluted with water (70 ml) and extracted with ethyl acetate (100 ml×2). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. A mixture of the residue, 2-amino-6-(methylamino)pyrimidin-4-ol (1.69 g, 6.00 mmol), potassium carbonate (50 mg) and dimethylsulfoxide (3 ml) was heated at 100° C. for 1 hour. After cooling, the mixture was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (1:1) to give 1.07 g (68%) of the title compound.

후처리

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. temperaturewas heated at 100° C. for 1 hour
  6. temperatureAfter cooling
  7. extractionextracted with ethyl acetate (100 ml×2)
  8. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel chromatography
  12. washeluting with hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-57ac30eac20147f4b6bfeed75f1714b3
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897607B2

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