Cyclopentanol → HCID 54596179, compound

HRID 57656Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[N:26]=3)=[CH:21][CH:20]=2)[N:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:38]1([OH:43])[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH:38]1([O:43][C:2]2[N:3]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[N:26]=4)=[CH:21][CH:20]=3)[N:4]=[C:5]3[C:10]=2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]3[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

Reactant 3

HCID 7298Cyclopentanol

HCID 10796Cesium carbonate

HCID 700947733-chloro-2-(4-(6-fluoropyridin-2-yl)benzyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 54596179HCID 54596179, compound

Conditions

Temperature: 150 °C

Procedure

3-chloro-2-(4-(6-fluoropyridin-2-yl)benzyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (20 mg, 0.045 mmol), cesium carbonate (22 mg, 0.068 mmol) and cyclopentanol (0.3 mL) are placed in a Biotage microwave vial. The vial is sealed, and then heated in a Biotage microwave instrument at 150° C. for 4 h. The reaction mixture is purified with a semi-preparative HPLC to give 10.4 mg of pure product as pale yellow solids (Purity: 97.7%). MS (ESI) m/z 492.2 [M+H]+.

Workup

customThe vial is sealed
customThe reaction mixture is purified with a semi-preparative HPLC

Sources & evidence

ORD record: ord-b3bd6d9ae61e4f69851556bf2212894a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434730B2

Reaction notes

Loading…