Ethanimidamide, acetate (1:1) → tert-Butyl 2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 132863

Reaction equation

HRID 132863 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.C(O)(=O)C.[C:23]([NH2:26])(=[NH:25])[CH3:24]>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C:2]2[N:25]=[C:23]([CH3:24])[N:26]=[CH:15][C:3]=2[CH2:4]1)=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 160356Ethanimidamide, acetate (1:1)HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 69223447tert-Butyl 2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Procedure

Reaction of tert-butyl 4-oxo-3-(dimethylaminomethylidene)-1-piperidinecarboxylate (1.15 g) from Intermediate 28, Step A with acetamidine acetate (0.54 g) according to the procedure described for Intermediate 28, Step B, and purification by flash chromatography (silica gel; 2% methanol/dichloromethane 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; 2% methanol/dichloromethane as eluant)

Sources & evidence

ORD record
ord-f99acf8cfdd64b2a8b8c1ee5cdb403f7
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Linked notes

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