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

HRID 1444597Notes

Reaction equation

HRID 1444597 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].[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].[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:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([Cl:19])[CH:21]=3)[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 69252Benzoyl chloride, 3-chloro-HCID 29184118tert-butyl 2-amino-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-6-carboxylate

Product 1

HCID 686786472-(3-chloro-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl esterYield 53.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 1202 mg (4.8 mmol) was added at 0° C. to a solution of 3-chlorobenzoic acid chloride 615 μl (4.8 mmol) in pyridine (25 ml) and stirring was performed for 2 h at 0° C. and then overnight 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-(3-chloro-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 790 mg (2.55 mmol, 53% of theoretical) was obtained.

Workup

  1. customovernight
  2. customat RT
  3. stirringstirring for 20 minutes
  4. extractionthe aqueous phase extracted with CH2Cl2 (3×20 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationAfter filtration and removal of the solvent, purification

Sources & evidence

ORD record
ord-4babe1ffc5094a258c42be64f5c757dc
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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