Sodium ethoxide → (s)-s-(4-{[4-{[(r)-2-Hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-s-cyclopropylsulfoximide

HRID 1169791Notes

Reaction equation

C(OC([N:6]=[S@@:7]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C@H:26]([CH3:29])[CH2:27][OH:28])[C:22]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)=[CH:21][N:20]=2)=[CH:14][CH:13]=1)([CH:9]1[CH2:11][CH2:10]1)=[O:8])=O)C.CC[O-].[Na+]>>[OH:28][CH2:27][C@H:26]([NH:25][C:23]1[C:22]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[CH:21][N:20]=[C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([S@@:7]([CH:9]3[CH2:11][CH2:10]3)(=[NH:6])=[O:8])=[CH:13][CH:14]=2)[N:24]=1)[CH3:29]

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 24769514(S)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide

Product 1

HCID 58985600(s)-s-(4-{[4-{[(r)-2-Hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-s-cyclopropylsulfoximideYield 63%

Procedure

In the reaction of (S)—N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]-amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide with sodium ethylate according to procedure 14, the desired product is obtained in 63% yield after chromatographic purification (silica gel, dichloromethane/ethanol (0-10% ethanol)).

Sources & evidence

ORD record: ord-90dcb0471c77490dbcd88630e2f1f61d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

Loading…