Allyl Alcohol → 4-i-Propyl-phenyl sulfamic acid-[6-allyloxy-5-(o-methoxyphenoxy)-2-(4-pyridyl)pyrimidin-4-yl]-amide

HRID 10249

Reaction equation

[CH2:1]([OH:4])[CH:2]=[CH2:3].C1COCC1.[H-].[Na+].Cl[C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:16]=[C:15]([NH:25][S:26](=[O:38])(=[O:37])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:14]=1[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47]>CN(C=O)C>[CH2:1]([O:4][C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)[N:16]=[C:15]([NH:25][S:26](=[O:37])(=[O:38])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:14]=1[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of allyl alcohol (1 ml) and THF (2 ml) was added sodium hydride (100 mg, 60% dispersion in mineral oil) followed by the addition of 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (100 mg, Referential Example 1e)). DMF (0.5 ml) was added and the reaction mixture was heated to 80° C. for 20 h. The solvents were evaporated, water (14 ml) and a 10% solution of citric acid was added until the pH was 3. The precipitate was filtered off and washed with water and purified by chromatography through silicagel with EtOAc/Hex=3:2 to give 4-i-propyl-phenyl sulfamic acid-[6-allyloxy-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (10 mg). tR=5.36 min, (LC); [M+H]+=548.46 (ES+).

Workup

customThe solvents were evaporated
additionwater (14 ml) and a 10% solution of citric acid was added until the pH was 3
filtrationThe precipitate was filtered off
washwashed with water
custompurified by chromatography through silicagel with EtOAc/Hex=3:2

Sources & evidence

ORD record: ord-a308b8d7315b46f3a3735372c111dddd
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094781B2

Linked notes

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