Trifluoroacetamidine → 6-(tert-Butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 132861

Reaction equation

HRID 132861 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C:3]1=[CH:15]N(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([NH2:23])=[NH:22]>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C:2]2[N:22]=[C:21]([C:20]([F:25])([F:24])[F:19])[N:23]=[CH:15][C:3]=2[CH2:4]1)=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 2776882TrifluoroacetamidineHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 692237216-(tert-Butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Procedure

Reaction of tert-butyl 4-oxo-3-(dimethylaminomethylidene)-1-piperidinecarboxylate (1.78 g) from Intermediate 28, Step A with trifluoroacetamidine (0.86 g) according to the procedure described for Intermediate 28, Step B, and purification by flash chromatography (silica gel; 18% ethyl acetate/hexanes as eluant), afforded the title compound as a viscous orange oil.

Workup

  1. customdescribed for Intermediate 28, Step B, and purification by flash chromatography (silica gel; 18% ethyl acetate/hexanes as eluant)

Sources & evidence

ORD record
ord-d24fb42fea5d4d20997ff53e5906c7c3
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Linked notes

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