Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1) → ethyl (RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyrate

HRID 34598Notes

Reaction equation

HRID 34598 reaction equation
Cl.[CH3:2][C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=[NH:5].CN(C)[CH:11]=[C:12]([CH:22]=O)[CH:13]([CH:19]([CH3:21])[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(OC=C(C=O)C(C(C)C)C(OCC)=O)C.C[O-].[Na+]>C(O)C>[CH3:2][C:3]([C:4]1[N:6]=[CH:11][C:12]([CH:13]([CH:19]([CH3:20])[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:22][N:5]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 53749266ethyl (RS)-4-ethoxy-3-formyl-2-(1-methylethyl)-3-butenoateHCID 54210763ethyl (RS)-4-dimethylamino-3-formyl-2-(1-methylethyl)-3-butenoate

Product 1

HCID 13911485ethyl (RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2,2-dimethylpropionamidine hydrochloride (0.14 g), prepared according to Example 1, was added to a solution of a 4:3 mixture of ethyl (RS)-4-dimethylamino-3-formyl-2-(1-methylethyl)-3-butenoate and ethyl (RS)-4-ethoxy-3-formyl- 2-(1-methylethyl)-3-butenoate (0.2 g), prepared according to the method of Example 10, in ethanol (2 cm3). A solution of sodium methoxide (0.06 g) in ethanol (1 cm3) was added to the stirred mixture, which was then heated at the reflux temperature for 2 hours. After cooling, the ethanol was evaporated under reduced pressure. The residual oil was purified by column chromatography on a silica gel support (Merck 7729), using dichloromethane, followed by dichloromethane containing 2% by volume ethyl acetate, as eluent, to give ethyl (RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyrate (0.068 g) as a pale yellow oil.

Workup

  1. customprepared
  2. temperaturewas then heated at the reflux temperature for 2 hours
  3. temperatureAfter cooling
  4. customthe ethanol was evaporated under reduced pressure
  5. customThe residual oil was purified by column chromatography on a silica gel support (Merck 7729)

Sources & evidence

ORD record
ord-19920ade6b34448d98ee16cc4e9b0e25
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

Loading…