Hydrochloric Acid → 4-(5-(3-Cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylbutanamide

HRID 2201212Notes

Reaction equation

C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.Cl.CC[N:22]([CH:26](C)C)C(C)C.[C:29]([C:31]1[CH:32]=[C:33]([C:37]2[N:38]([CH2:50][CH2:51][CH2:52][C:53]([O-])=[O:54])[CH:39]=[C:40]3[C:45]=2[C:44](=[O:46])[N:43]([CH3:47])[C:42](=[O:48])[N:41]3[CH3:49])[CH:34]=[CH:35][CH:36]=1)#[N:30].[Li+].CN([CH:60]=[O:61])C>>[C:29]([C:31]1[CH:32]=[C:33]([C:37]2[N:38]([CH2:50][CH2:51][CH2:52][C:53]([N:22]([O:61][CH3:60])[CH3:26])=[O:54])[CH:39]=[C:40]3[C:45]=2[C:44](=[O:46])[N:43]([CH3:47])[C:42](=[O:48])[N:41]3[CH3:49])[CH:34]=[CH:35][CH:36]=1)#[N:30]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 111923Propylphosphonic anhydride

HCID 86723451Lithium 4-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate

Product 1

HCID 867234524-(5-(3-Cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylbutanamide

Procedure

T3P® (31.3 ml, 52.6 mmol) was added dropwise to a solution of N,O-dimethyllhydroxylamine hydrochloride (2.70 g, 27.6 mmol), DIPEA (18.39 ml, 105 mmol) and lithium 4-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate (9.8 g, 26.3 mmol) in DMF (263 mL). The mixture was stirred at room temperature for 40 minutes and quenched with water (250 mL). The resultant precipitate was collected by filtration under reduced pressure to afford the title compound.

Workup

customquenched with water (250 mL)
filtrationThe resultant precipitate was collected by filtration under reduced pressure

Sources & evidence

ORD record: ord-f03ca06b77654e51b53e50b8de2d2f4e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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