Potassium Carbonate → Methyl 1-{[(4-tert-butoxy-4-oxobutyl)amino]carbonyl}-6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylate

HRID 1452656Notes

Reaction equation

HRID 1452656 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14](OC3C=CC([N+]([O-])=O)=CC=3)=[O:15])[C:12]([O:26][CH3:27])=[N:11][C:10]([CH3:28])=[C:9]2[C:29]([O:31][CH3:32])=[O:30])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CO.C(Cl)Cl>[C:46]([O:45][C:43](=[O:44])[CH2:42][CH2:41][CH2:40][NH:39][C:14]([N:13]1[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([C:29]([O:31][CH3:32])=[O:30])=[C:10]([CH3:28])[N:11]=[C:12]1[O:26][CH3:27])=[O:15])([CH3:49])([CH3:47])[CH3:48]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7020335Tert-butyl 4-aminobutanoateHCID 105272225-Methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate

Product 1

HCID 57526926Methyl 1-{[(4-tert-butoxy-4-oxobutyl)amino]carbonyl}-6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylateYield 99,460.797%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate (88.7 mg, 0.200 mmol) and K2CO3 (41.5 mg, 0.300 mmol) in CH3OH/CH2Cl2 (0.1/2.0 mL) was added tert-butyl 4-aminobutanoate (31.8 mg, 0.200 mmol). After stirring at rt for 1 h, the mixture was washed with saturated Na2CO3 and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (5%-10% 2 M NH3/MeOH in 50% EtOAc/Hexanes) to afford the product (92.2 g, 99%). mp 135-138° C.; 1H NMR (CD3OD) δ 7.29-7.23 (m, 2H), 6.97-6.88 (m, 2H), 6.65 (s, 1H), 3.98 (s, 3H), 3.66 (s, 3H), 3.38-3.30 (m, 2H), 2.43 (s, 3H), 2.28 (t, 2H, J=7.2 Hz), 1.89-1.78 (m, 2H), 1.43 (s, 9H); ESMS m/e: 464.1 (M+H)+.

Workup

  1. washthe mixture was washed with saturated Na2CO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (5%-10% 2 M NH3/MeOH in 50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b64e2269090249d6a98b85ff01f2ab93
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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