Sodium Hydroxide → 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzamide

HRID 38359Notes

Reaction equation

[NH:1]1C=CN=[C:2]1[C:6]1[C:7]([O:24][CH3:25])=[CH:8][C:9]([CH:21]([CH3:23])[CH3:22])=[C:10]([CH:20]=1)[O:11][C:12]1[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=1.[OH-:26].[Na+]>C(O)C>[NH2:18][C:15]1[N:14]=[C:13]([NH2:19])[C:12]([O:11][C:10]2[C:9]([CH:21]([CH3:23])[CH3:22])=[CH:8][C:7]([O:24][CH3:25])=[C:6]([CH:20]=2)[C:2]([NH2:1])=[O:26])=[CH:17][N:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To 5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile (49 mg, 0.16 mmol, from Example 15) suspended in ethanol (1 mL) was added sodium hydroxide (64 mg, 1.60 mmol, dissolved in 1 mL water). The reaction was heated at 110° C. for 5 hours, cooled, and washed with dichloromethane (25 mL). The dichloromethane layer was concentrated and purified by preparatory TLC plates (92/8/0.5 dichloromethane/methanol/ammonium hydroxide) to yield 5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzamide as white solid (9 mg, 17%, MS (M+H)=318), which was converted to the hydrochloride salt.

Workup

temperaturecooled
washwashed with dichloromethane (25 mL)
concentrationThe dichloromethane layer was concentrated
custompurified by preparatory TLC plates (92/8/0.5 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record: ord-7c93a7a6823f4d729dc8ec30837b660c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524725B2

Reaction notes

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