1,2-Dimethoxyethane → HCID 89629895, compound

HRID 882174Notes

Reaction equation

HRID 882174 reaction equation
C([N:4]([C:6]([C:8]1[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=O)[NH2:5])(=O)C.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:35].CO[CH2:50][CH2:51]OC>>[CH3:50][C:51]1[S:35][C:6]([C:8]2[C:16]3[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=2)=[N:4][N:5]=1

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 14817Phosphorus sulfide (P2S5)HCID 131732647HCID 131732647, compound

Product 1

HCID 89629895HCID 89629895, compound

Conditions

Temperature
50 °C

Procedure

To a solution of N-acetyl-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide (0.40 g, 0.85 mmol) in ethylene glycol dimethyl ether (10 mL), was added P2S5 (378 mg, 1.70 mmol). The resulting solution was stirred for 1 hour at 50° C., then concentrated in vacuo and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-100% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 2-methyl-5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,3,4-thiadiazole as a yellow oil. LRMS (ESI) calc'd for C21H25N6O3SSi [M+H]+: 469, found 469.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was purified by chromatography
  8. washeluting with 1-100% ethyl acetate/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2b3fb2c939f478686f3208741e7d6a9
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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