반응 #92573

반응 방정식

7-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

DMSO

NaOH

H2O2

→

TFA

수율 64.0%

7-(Aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

수율 64.0%

용매

EtOH

반응 조건

후처리

1. 1
   농축the mixture was concentrated
2. 2
   기타to remove EtOH
3. 3
   기타The residue was partitioned between water (30 mL) and EA (20 mL)
4. 4
   농축The organic phase was concentrated
5. 5
   기타purified
6. 6
   세척by pre-HPLC eluting from 20% to 40% CH3CN in 0.1% TFA in H2O
7. 7
   workup.ADDITIONFractions containing the desired product
8. 8
   workup.WAITlyophilized overnight

실험 절차

To a solution of 7-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (15 mg, 0.043 mmol) in 2 mL of EtOH was added 1 mL of DMSO, 0.5 mL of NaOH (5N) and 0.5 mL of H2O2 (30% aqueous solution). After stirring at 60° C. for 2 hr, the mixture was concentrated to remove EtOH. The residue was partitioned between water (30 mL) and EA (20 mL). The organic phase was concentrated and purified by pre-HPLC eluting from 20% to 40% CH3CN in 0.1% TFA in H2O. Fractions containing the desired product were combined and lyophilized overnight to give the product as a TFA salt (10 mg, 64%). 1H NMR (400 MHz, DMSO-d6) δ 8.07 (br s, 3H), 7.62 (d, J=8.8 Hz, 2H), 7.43-7.35 (m, 2H), 7.25 (t, J=7.6 Hz, 1H), 7.15-7.12 (m, 4H), 6.77 (br s, 1H), 4.38-4.30 (m, 1H), 3.40-3.20 (m, 4H), 2.16-2.06 (m, 1H), 2.00-1.80 (m, 1H). MS (ESI) m/e [M+1]+364.0.

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