Potassium Carbonate → HCID 11305407, compound

HRID 1172564Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:27][N:7]2[CH2:8][CH2:9][N:10]([C:12]3[N:17]=[C:16]([NH2:18])[N:15]4[N:19]=[C:20]([C:22]5[O:23][CH:24]=[CH:25][CH:26]=5)[N:21]=[C:14]4[N:13]=3)[CH2:11][CH:6]2[CH2:5][CH2:4]1.Cl[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[N:21]=[C:14]2[N:13]=[C:12]([N:10]3[CH2:9][CH2:8][N:7]4[CH2:27][CH:3]([CH2:2][NH:1][C:29]5[N:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[CH2:4][CH2:5][CH:6]4[CH2:11]3)[N:17]=[C:16]([NH2:18])[N:15]2[N:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of (7RS,9aRS)—S-(7-aminomethyl-octahydro-pyrido[1,2-a]pyrazin-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (1 eq.; see Example 9 above) and 2-chloropyrimidine (2 eq.) in DMSO was treated with K2CO3 (2 eq.). The mixture was stirred at around 85° C. for 4 hours. The reaction mixture was then filtered, and the filtrate was concentrated and purified by preparative HPLC using aqueous CH3CN (buffered with 0.1% TFA) to afford (7RS,9aRS)-2-furan-2-yl-5-[7-(pyrimidin-2-ylaminomethyl)-octahydro-pyrido[1,2-a]pyrazin-2-yl]-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine as a white powder: 1H NMR (400 MHz, DMSO-d6) δ 1.60-1.86 (m, 4H), 2.21-2.30 (bs, 1H), 3.05-3.32 (m, 4H), 3.33-3.52 (m, 4H), 3.56-3.72 (m, 1H), 4.62-4.83 (m, 2H), 6.63 (t, J=4.8 Hz, 1H), 6.69 (dd, J=1.8, 3.4 Hz, 1H), 7.08 (d, J=3.4 Hz, 1H), 7.41 (t, J=5.6 Hz, 1H), 7.89 (d, J=1.8 Hz, 1H), 8.32 (d, J=4.8 Hz, 2H), 8.40-8.65 (m, 2H). MS m/z: 448 [M+H]+.

Workup

filtrationThe reaction mixture was then filtered
concentrationthe filtrate was concentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e0649de05c464512ba4c5bbb0b96bb59
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834014B2

Reaction notes

Loading…