Dichloromethane → 2-(2-ethoxy-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

HRID 1444595Notes

Reaction equation

HRID 1444595 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[C:13]([NH2:16])[N:14]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])[CH3:20].[OH-].[Na+].C(Cl)Cl>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[C:13]([NH:16][C:24](=[O:25])[C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[O:21][CH2:19][CH3:20])[N:14]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 30163972-Ethoxybenzoyl chlorideHCID 29184118tert-Butyl 2-amino-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 686797542-(2-ethoxy-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 528 mg (2.11 mmol) was added at 0° C. to a solution of 2-ethoxybenzoic acid chloride 390 mg (2.11 mmol) in pyridine (25 ml) and stirring was performed for 2 h at 0° C. and then for 72 h at RT under nitrogen as inert gas. After the addition of aqueous 1 M NaOH (40 ml) and stirring for 20 minutes, CH2Cl2 (50 ml) was added and the aqueous phase extracted with CH2Cl2 (3×20 ml). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent, purification was performed by means of column chromatography and the product 2-(2-ethoxy-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 600 mg (1.51 mmol, 72% of theoretical) was obtained.

Workup

  1. waitfor 72 h at RT under nitrogen as inert gas
  2. stirringstirring for 20 minutes
  3. extractionthe aqueous phase extracted with CH2Cl2 (3×20 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationAfter filtration and removal of the solvent, purification

Sources & evidence

ORD record
ord-111f58f833294051a1f54be3d18747eb
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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