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

HRID 1692763Notes

Reaction equation

HRID 1692763 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-6c34a8b5e5374e9d884698da1a35db89
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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