Triethylamine → HCID 58459065, compound

HRID 408825Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[N:6]2[CH2:12][CH2:13][OH:14].[CH2:22]1[NH:27][CH2:26][CH2:25][N:24]2[C:28](=[O:31])[CH2:29][CH2:30][CH:23]12.C(N(CC)CC)C>C(O)C>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:5]1[N:6]([CH2:12][CH2:13][OH:14])[C:7]2[C:3]([N:4]=1)=[C:2]([N:27]1[CH2:26][CH2:25][N:24]3[C:28](=[O:31])[CH2:29][CH2:30][CH:23]3[CH2:22]1)[N:10]=[C:9]([CH3:11])[N:8]=2

Participants

Conditions

Temperature: 82.5 °C

Procedure

Charge a 500 mL three necked round bottomed flask with 2-[6-chloro-8-(2-chlorophenyl)-2-methyl-purin-9-yl]ethanol (13.3 g, 0.0412 mmol) and ethanol (200 mL), followed by 2,3,4,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-6-one (6.365 g, 0.0453 mol) and triethylamine (14.8 mL, 3.5 eq). Heat the mixture to 80-85° C. for 24 h. Cool the reaction to room temperature and concentrate under vacuum to give a yellow solid as the crude product. Purify the crude material by column chromatography, using 400 g of silica gel and eluting with dichloromethane/methanol (50:1), to give the product as a yellow solid (13.3 g). 1H NMR (dmso-d6): δ 7.55-7.41 (m, 4H); 5.72 (bs, 2H); 4.16-3.92 (m, 3H); 3.71 (s, 2H); 3.71-3.68 (m, 1H); 3.02-2.93 (m, 2H); 2.74 (m, 1H); 2.70 (s, 3H); 2.44 (m, 2H); 2.32-2.29 (m, 1H); 1.76-1.69 (m, 1H).

Workup

temperatureCool
customthe reaction to room temperature
concentrationconcentrate under vacuum
customto give a yellow solid as the crude product
customPurify the crude material by column chromatography
washeluting with dichloromethane/methanol (50:1)

Sources & evidence

ORD record: ord-41380d3c89be47ceb12ccaddf41f1ec7
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759360B2

Reaction notes

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