Sodium Hydroxide → HCID 11443875, compound

HRID 2422156Notes

Reaction equation

[CH3:1][N:2]([CH3:40])[C:3]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[C:7]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:6]=[C:5]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[O:29])=[CH:23][CH:22]=2)[N:4]=1.[OH-].[Na+]>CO>[CH3:40][N:2]([CH3:1])[C:3]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[C:7]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:6]=[C:5]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[O:29])=[CH:25][CH:26]=2)[N:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl {4-(dimethylamino)-6-morpholin-4-yl-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.096 g, 0.18 mmol) in MeOH (2 mL) at room temperature was treated with 1N NaOH (1 mL) and the resulting mixture was heated at 60° C. for 5 hours. After cooling to room temperature, the volatiles were removed under reduced pressure and the remaining aqueous layer was washed with Et2O and acidified with 1N HCl. The separated solids were collected by suction, rinsed with water, and dried under vacuum to give {4-(dimethylamino)-6-morpholin-4-yl-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetic acid (0.059 g, 64% yield) as a white solid.

Workup

temperatureAfter cooling to room temperature
customthe volatiles were removed under reduced pressure
washthe remaining aqueous layer was washed with Et2O
customThe separated solids were collected by suction
washrinsed with water
customdried under vacuum

Sources & evidence

ORD record: ord-29f52d8f60d049da92f0cbd342d2500a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960393B2

Reaction notes

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