2-(1-Chloroethyl)-5-fluoropyridine → (2R)-2-[(2-Amino-5-{[1-(5-fluoropyridin-2-yl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol

HRID 1694539Notes

Reaction equation

HRID 1694539 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[CH:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][CH:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 591868842-(1-Chloroethyl)-5-fluoropyridineHCID 178445911HCID 178445911, compound

Product 1

HCID 25064756(2R)-2-[(2-Amino-5-{[1-(5-fluoropyridin-2-yl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-olYield 21%

Procedure

The title compound was prepared according to General method A starting from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (21 mg, 0.072 mmol) and 2-(1-chloroethyl)-5-fluoropyridine (8 mg, 0.048 mmol). Purification by preparative HPLC yielded 4 mg (21% yield) of the title compound as a mixture of diastereomers.

Workup

  1. customThe title compound was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-73541387d2144f4285acd283cc46d49f
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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