Benzyl mercaptan → Tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

HRID 624705Notes

Reaction equation

HRID 624705 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]1[CH:16]=[C:15]([N:17]([CH:25]2[CH2:27][CH2:26]2)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:14]2[N:28]=[CH:29][C:30]([CH:31]=[O:32])=[C:13]2[N:12]=1.[CH2:33]([SH:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C>[CH2:33]([S:40][C:11]1[CH:16]=[C:15]([N:17]([CH:25]2[CH2:27][CH2:26]2)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:14]2[N:28]=[CH:29][C:30]([CH:31]=[O:32])=[C:13]2[N:12]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 58196421Tert-butyl 5-chloro-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

Product 1

HCID 86714600Tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamateYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diisopropylethylamine (256 μL, 1.48 mmol) was added to tert-butyl 5-chloro-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (250 mg, 0.74 mmol) suspended in ethanol (2.5 mL). Benzyl mercaptan (191 μL, 1.48 mmol) was added and the reaction was homogeneous after ˜2 min. After 10 min, the reaction was diluted with ethanol (3 mL) and the precipitate was filtered and washed with ethanol (10 mL) to yield tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (148 mg, 47%). LCMS (ES): >95% pure, m/z 425 [M+1]+.

Workup

  1. waitAfter 10 min
  2. filtrationthe precipitate was filtered
  3. washwashed with ethanol (10 mL)

Sources & evidence

ORD record
ord-cea709df1dd14c65bd9f88b0f52ddc02
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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