Picolyl chloride hydrochloride → 2-(1-benzothien-3-ylmethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-5-(pyridin-2-ylmethyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181824Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:19]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[C:18]3[C:13]([N:14]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:15](=[O:27])[NH:16][C:17]3=[O:26])=[N:12]2)=[CH:2]1.N12C[CH2:41][CH2:40][N:39]=[C:38]1[CH2:37][CH2:36][CH2:35]CC2.Cl.N1C=CC=CC=1CCl>CS(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:19]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[C:18]3[C:13]([N:14]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:15](=[O:27])[N:16]([CH2:41][C:40]4[CH:35]=[CH:36][CH:37]=[CH:38][N:39]=4)[C:17]3=[O:26])=[N:12]2)=[CH:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(1-benzothien-3-ylmethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was dissolved in anhydrous dimethylsulfoxide and 1,8-diazabicyclo[5.4.0]undec-7-ene was added. 2-picolyl chloride hydrochloride was added and the mixture was heated at 80° C. for 18 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trifluoroacetic acid mixtures. 525 (M+H).

Workup

customThe crude reaction product
customwas purified by semi-prep RPHPLC
washeluting with water/acetonitrile/trifluoroacetic acid mixtures

Sources & evidence

ORD record: ord-4ff36ad55c3042099a6f4b7643667292
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285558B2

Reaction notes

Loading…