Methanol → HCID 69652905, compound

HRID 2181600Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([CH:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[N:3]=1.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[NH4+].[OH-].CO>CCO.CCOC(C)=O>[N:26]1([C:2]2[N:10]=[C:9]3[C:5]([NH:6][CH:7]=[N:8]3)=[C:4]([CH:11]3[CH2:16][NH:15][CH2:14][CH2:13][N:12]3[C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[N:3]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 145 °C

Procedure

2-Chloro-6-[N-(trimethylsilylethoxycarbonyl)piperazinyl] purine (17.10 g, 44.66 mmol) and piperazine (23.08 g, 268 mmol) were suspended in EtOH (200 mL) in a bomb reactor. The bomb reactor was heated to 145° C. for 24 hours. The reaction progress was monitored by thin layer chromatography NH4OH:MeOH:EtOAc (5/5/90, v/v/v) which showed disappearance of starting material and formation of a new product spot after 24 hours. The EtOH was evaporated and water (700 mL) was added to the residue. The resulting precipitate was filtered and dried in a vacuum oven at 110° C. for 24 hours to give 18.5 g (96%) of the title compound. 1H NMR (CDCl3): δ 0.02 (s, 9H), 1.01 (t, 2H), 2.99 (bs, 4H), 3.61 (bs, 4H), 3.74 (bs, 6H), 4.23 (bm, 6H), 7.59 (s, 1H).

Workup

customafter 24 hours
customThe EtOH was evaporated
additionwater (700 mL) was added to the residue
filtrationThe resulting precipitate was filtered
customdried in a vacuum oven at 110° C. for 24 hours

Sources & evidence

ORD record: ord-e34013f7a67242e193d9e7e59023efc8
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06893815B1

Reaction notes

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