Carbonate Ion → 6-[(cyclopropylmethyl)(propyl)amino]-N-{2-methyl-4-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyrimidine-4-carboxamide

HRID 1746768Notes

Reaction equation

HRID 1746768 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.Cl.[NH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]C(C)(C)C)=O.C(=O)([O-])[O-].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:28]4[CH2:29][CH2:30][CH2:31][C:32]4=[O:34])=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 19660Carbonate IonHCID 2724942TriacetoxyborohydrideHCID 24750478Tert-butyl 4-aminobutanoate hydrochlorideHCID 59446872HCID 59446872, compound2×

Product 1

HCID 251830666-[(cyclopropylmethyl)(propyl)amino]-N-{2-methyl-4-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyrimidine-4-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-((cyclopropylmethyl)(propyl)amino)-N-(4-formyl-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 29, 100 mg; 0.28 mmol) in DCM (5 ml) was treated with tert-butyl 4-aminobutanoate hydrochloride (Bachem, 244.6 mg; 1.25 mmol) and polymer supported carbonate (150 mg) followed by polymer supported triacetoxy borohydride (150 mg). After stirring for 18 hours the mixture was filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid (85 mg, 70%).

Workup

  1. filtrationwas filtered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography (silica)
  4. washeluting with petroleum ether containing
  5. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-86b12a104efc4fac9be243a4362cff92
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

Loading…