Ethanol → [(2R)-2-[[2-amino-5-[[(3-chloro-2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]propyl]carbamic acid, 1,1-dimethylethyl ester

HRID 1097355Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:8][C:7](S(CC3C=CC=CC=3)(=O)=O)=[N:6][C:5]=2[N:32]=1.[Cl:33][C:34]1[C:35]([F:42])=[C:36]([CH2:40][SH:41])[CH:37]=[CH:38][CH:39]=1.C(O)C.[BH4-].[Na+]>CS(C)=O>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[N:8][C:7]([S:41][CH2:40][C:36]3[CH:37]=[CH:38][CH:39]=[C:34]([Cl:33])[C:35]=3[F:42])=[N:6][C:5]=2[N:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of the product from example 25 step f) (1.2 g), the product from example 25 step g) (1.6 g) in a mixed solvent of ethanol (30 ml) and DMSO (5 ml) was added sodium borohydride (100 mg) and the mixture heated at 50° C. for 2 hours. The ethanol was removed by rotary evaporation and the crude product extracted into ethyl acetate and washed with water. The subtitle compound was obtained by purification (SiO2, 1:1)dichloromethane:ethyl acetate as eluant) to give (1.95 g).

Workup

customThe ethanol was removed by rotary evaporation
extractionthe crude product extracted into ethyl acetate
washwashed with water

Sources & evidence

ORD record: ord-a99eaf29ab024fe899b1c10f551be520
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143261B2

Reaction notes

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