Diisopropylethylamine → (2R)-2-[[2-Amino-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol

HRID 968206Notes

Reaction equation

HRID 968206 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([SH:15])=[N:6][C:5]=2[N:16]=1.Cl.Cl[CH2:19][C:20]1[N:21]=[C:22]([CH3:25])[S:23][CH:24]=1.CCN(C(C)C)C(C)C>CS(C)=O.CN1C(=O)CCC1>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([S:15][CH2:19][C:20]3[N:21]=[C:22]([CH3:25])[S:23][CH:24]=3)=[N:6][C:5]=2[N:16]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 178461804HCID 178461804, compound

Product 1

HCID 9969306(2R)-2-[[2-Amino-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanolYield 36.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred solution of the product of step (b) (0.05 g) in DMSO (4 ml) was treated with a solution of 4-chloromethyl-2-methylthiazole hydrochloride (0.029 g) and Hunig's base (0.025 g) in NMP (0.5 ml) and stirred for 1 hour. The solution was purified by reverse phase preparative HPLC on Nova-pak® C18 column, using 10 to 60% acetonitrile in 0.1% aqueous ammonium acetate at 50 ml/min over 10 min to give the titled compound (0.021 g)

Workup

  1. customThe solution was purified by reverse phase preparative HPLC on Nova-pak® C18 column
  2. customover 10 min

Sources & evidence

ORD record
ord-07d9138d02334892af985f62ce52fa1b
Source dataset
uspto-grants-2005_10
Patent number
US06958343B2

Reaction notes

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