Citric Acid → Benzylsulfamic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide

HRID 10260Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][S:11](=[O:21])(=[O:20])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30].C(O)(=O)C[C:33](CC(O)=O)([C:35](O)=[O:36])[OH:34]>C(O)CO>[OH:34][CH2:33][CH2:35][O:36][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][S:11](=[O:21])(=[O:20])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

Benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide (1.75 g) was added to a solution of potassium tert.-butylate (1.87 g) in ethylene glycol (30 ml) and stirred at 100° C. for 40 h. The reaction mixture was poured onto water (120 ml), acidified with solid citric acid (1.9 g) and cooled to 0° C. The precipitate was filtered off, washed with water and dried at HV to give benzylsulfamic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide (Example 203). LC-MS: tR=4.70; [M+H]+=493.09.

Workup

additionThe reaction mixture was poured onto water (120 ml)
temperaturecooled to 0° C
filtrationThe precipitate was filtered off
washwashed with water
customdried at HV

Sources & evidence

ORD record: ord-6ee78f80b18e4ed883b42873c9de4f88
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094781B2

Reaction notes

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