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

HRID 1169792Notes

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]([CH2:29][OH:30])[CH2:27][CH3:28])[C:22]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=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:30][CH2:29][C@H:26]([NH:25][C:23]1[C:22]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)=[CH:21][N:20]=[C:19]([NH:18][C:15]2[CH:14]=[CH:13][C:12]([S@:7]([CH:9]3[CH2:11][CH2:10]3)(=[NH:6])=[O:8])=[CH:17][CH:16]=2)[N:24]=1)[CH2:27][CH3:28]

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 24769515(R)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide

Product 1

HCID 58985571(r)-s-(4-{[4-{[(r)-1-(Hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-s-cyclopropylsulfoximideYield 81%

Procedure

In the reaction of (R)—N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-1-(hydroxymethyl)propyl]-amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide with sodium ethylate according to procedure 14, the desired product is obtained in 81% yield after chromatographic purification (silica gel, dichloromethane/ethanol (0-10% ethanol)).

Sources & evidence

ORD record: ord-f7ed61c76e864a0a96ad373403452941
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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