Potassium Acetate → HCID 24970006, compound

HRID 2262041Notes

Reaction equation

HRID 2262041 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[O:10][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[N:32][NH:33]3)O1.C([O-])(=O)C.[K+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:33]1[C:34]2[C:30](=[C:29]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[O:10][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:37]=[CH:36][CH:35]=2)[CH:31]=[N:32]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59593058HCID 59593058, compound

Product 1

HCID 24970006HCID 24970006, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

2-(2-chloro-4-morpholinofuro[3,2-d]pyrimidin-6-yl)propan-2-ol (60 mg, 1.0 eq) was dissolved in acetonitrile (2.0 ml) and treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (123 mg, 2.5 eq), PdCl2(PPh3)2 (14.1 mg, 0.10 eq) and 1M potassium acetate (0.6 ml). The vial was sealed and heated with stirring in the microwave to 140° C. for 30 minutes. The crude reaction mixture was concentrated and purified by reverse phase HPLC to afford 2-(2-(1H-indazol-4-yl)-4-morpholinofuro[3,2-d]pyrimidin-6-yl)propan-2-ol 107. MS (Q1) 380 (M)+.

Workup

  1. customThe vial was sealed
  2. temperatureheated
  3. customThe crude reaction mixture
  4. concentrationwas concentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4a3ef93ea68c401c9db13d5611b829bb
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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