Sodium Hydroxide → HCID 10254245, compound

HRID 1348808Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[NH:18][C:19]([CH:21]1[CH2:26][CH2:25][NH:24][C:23](=[O:27])[N:22]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)CO>[CH2:1]([N:8]1[C:9](=[O:10])[C:11]2[C:12](=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:18]=[C:19]1[CH:21]1[CH2:26][CH2:25][NH:24][C:23](=[O:27])[N:22]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Formula I where R1, R2, R4, R6, R7, R8 and R9 are H, R3 is Chloro; R5 is Benzyl; R10 is p-Methyl-benzyl; and V is N—R′″ where R′″ is H: 3-(4-Methyl-benzyl)-2-oxo-hexahydro-pyrimidine-4-carboxylic acid (2-benzylcarbamoyl-5-chloro-phenyl)-amide (350 mg, 0.713 mmol) was dissolved in 60 mL of ethylene glycol to which was added sodium hydroxide (60 mg, 1.5 mmol). The mixture was stirred at 140° C. for 20 hours and monitored by LC-MS. Following consumption of starting material, the reaction mixture was poured into 100 mL of water. After extraction with DCM, the crude product was purified by flash silica gel chromatography (stepwise gradient 1:4, 1:2, 1:1, 2:1, 4:1 with ethyl acetate:hexanes as eluent) to give the desired product of Formula I, 3-benzyl-7-chloro-2-[3-(4-methyl-benzyl)-2-oxo-hexahydro-pyrimidin-4-yl]-3H-quinazolin-4-one (180 mg, 53%).

Workup

customconsumption of starting material
additionthe reaction mixture was poured into 100 mL of water
extractionAfter extraction with DCM
customthe crude product was purified by flash silica gel chromatography (stepwise gradient 1:4, 1:2, 1:1, 2:1, 4:1 with ethyl acetate

Sources & evidence

ORD record: ord-309f48bb583a40bead10db37f8315f4d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211580B2

Reaction notes

Loading…