Dimethylamine → HCID 86723515, compound

HRID 2201277Notes

Reaction equation

CS(O[CH2:6][C@H:7]([N:29]1[C:37]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:36]2[C:31]([N:32]([CH3:47])[C:33](=[O:46])[N:34]([CH3:45])[C:35]2=[O:44])=[CH:30]1)[CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.[CH3:48][NH:49][CH3:50]>CN(C=O)C.CCOC(C)=O>[CH3:48][N:49]([CH2:6][C@H:7]([N:29]1[C:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[C:36]2[C:31]([N:32]([CH3:47])[C:33](=[O:46])[N:34]([CH3:45])[C:35]2=[O:44])=[CH:30]1)[CH2:8][S:9][C:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:50]

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-3-(tritylthio)propyl methanesulfonate (step 3)(1.7 g, 2.55 mmol) was dissolved in DMF (12 mL) and dimethylamine (40% wt. aqueous solution) (1.455 mL, 11.49 mmol) was added. The mixture was heated under microwave irradiation at 120° C. for 15 h. The reaction mixture was diluted with EtOAc and washed with brine (4×). The organic phase was dried over sodium sulphate and evaporated under vacuum. The residue was redissolved in DCM and evaporated onto silica. Purification by chromatography on silica, eluting with 20-100% EtOAc in iso-hexane gave the title compound.

Workup

washwashed with brine (4×)
dry with materialThe organic phase was dried over sodium sulphate
customevaporated under vacuum
dissolutionThe residue was redissolved in DCM
customevaporated onto silica
customPurification by chromatography on silica
washeluting with 20-100% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-41eb3ed8ef2d4e41a6f96d4bfc126a4d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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