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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 2201212
Notes
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Reaction equation

HRID 2201212 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 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 86723452
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

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

  1. customquenched with water (250 mL)
  2. 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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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes