Trifluoroacetic acid → 5-(2-(2-methoxypropan-2-yl)-7-morpholinothiazolo[5,4-d]pyrimidin-5-yl)-N-methylpyridin-2-amine

HRID 1365786Notes

Reaction equation

HRID 1365786 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[N:10]=[C:9]([C:11]([O:14][CH3:15])([CH3:13])[CH3:12])[S:8][C:6]=2[N:7]=1.[CH3:22][N:23]([C:31]1[CH:36]=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][N:32]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:15][O:14][C:11]([C:9]1[S:8][C:6]2[N:7]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([NH:23][CH3:22])=[N:32][CH:33]=3)[N:3]=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:5]=2[N:10]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 445416766-(Boc-methylamino)pyridine-3-boronic acid pinacol esterHCID 866300674-(5-Chloro-2-(2-methoxypropan-2-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 252538365-(2-(2-methoxypropan-2-yl)-7-morpholinothiazolo[5,4-d]pyrimidin-5-yl)-N-methylpyridin-2-amine

Procedure

Crude 4-(5-chloro-2-(2-methoxypropan-2-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine (60 mg) was reacted with tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate via general procedure A. This crude product was then treated with TFA to remove residual protecting group and purified via reverse phase HPLC to get 58.4 mg 102. MS (Q1) 401.2 (M)+.

Workup

  1. customto remove residual
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-ded40f18689c463fb0c60716cff1253f
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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