Isopropanol → HCID 21098057, compound

HRID 1351163Notes

Reaction equation

C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(O)(C)C.[Cl:36][C:37]1[C:45]2[C:40](=[N:41][C:42]([S:46][CH3:47])=[N:43][CH:44]=2)[NH:39][N:38]=1>C1COCC1>[Cl:36][C:37]1[C:45]2[C:40](=[N:41][C:42]([S:46][CH3:47])=[N:43][CH:44]=2)[N:39]([CH:19]([CH3:18])[CH3:14])[N:38]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Triphenylphosphine (387 mg, 1.5 mmol) was dissolved in THF (15 mL) and the solution was cooled to −78° C. Diethyl azodicarboxylate (225 uL, 1.5 mmol) was added slowly to the reaction mixture. The reaction was stirred for 5 min and then isopropanol was added (115 uL, 1.5 mmol) dropwise. After stirring an additional 5 min. the 3-Chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (305 mg, 1.6 mmol) was added as a solid. The resulting suspension was kept at −78° C. for 5 min then the cooling bath was removed. The reaction was stirred for 3 hours at room temperature. After concentration the desired 3-Chloro-1-isopropyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine was obtained by column chromotography (0–5% MeOH/methylene chloride); 1H-NMR (CDCl3): • 1.46 (d, 1H), 2.66 (s, 3H), 4.53 (q, 6H), 8.87 (s, 1H); LC/MS (m/e)=243.0 (MH+), Rt=2.25 min.

Workup

additionwas added as a solid
waitThe resulting suspension was kept at −78° C. for 5 min
customthe cooling bath was removed
stirringThe reaction was stirred for 3 hours at room temperature
concentrationAfter concentration the desired 3-Chloro-1-isopropyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
customwas obtained by column chromotography (0–5% MeOH/methylene chloride)

Sources & evidence

ORD record: ord-dc0bab1680394ab68d777e29833a9bd3
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217710B2

Reaction notes

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