4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole → HCID 86653098, compound

HRID 2262207Notes

Reaction equation

HRID 2262207 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[O:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1>C([O-])([O-])=O.[Na+].[Na+].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>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([C:21]3[CH:20]=[N:19][O:18][CH:22]=3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 164141804-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazoleHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86653098HCID 86653098, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 (150 mg), 84 mg of 4-isoxazoleboronic acid pinacol ester and 14 mg of bis(triphenylphosphine)palladium(II) dichloride in 0.7 mL of 1M Na2CO3 aqueous solution and 0.7 mL of acetonitrile was heated to 100° C. in a sealed microwave reactor for 10 min. The reaction mixture was evaporated. The crude product was purified by flash chromatography eluting with 0-20% MeOH/DCM to yield 2-chloro-6-(isoxazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidine (85 mg, 67%).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 0-20% MeOH/DCM

Sources & evidence

ORD record
ord-e8bce85700f945f18e995c3456c46e06
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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