1,4-Dioxane → HCID 69939278, compound

HRID 244009Notes

Reaction equation

HRID 244009 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([CH:17]=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1)CCC.O1[CH2:43][CH2:42]OCC1>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([C:17]([C:1]4[C:2]([C:24]5[N:25]=[CH:26][CH:27]=[CH:28][N:29]=5)=[N:3][CH:4]=[CH:42][CH:43]=4)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:5]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 27632512-(Tributylstannyl)pyrimidineHCID 86669170HCID 86669170, compound

Product 1

HCID 69939278HCID 69939278, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 2-bromopyridin-3-yl)(5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (Example 234) (50 mg, 0.14 mmol), 2-tributylstannylpyrimidine (50 mg, 0.14 mmol), and copper iodide (2.6 mg, 0.014 mmol) in 1,4 dioxane (1 mL) was added Pd(PPh3)4 (16 mg, 0.014 mmol). The reaction was irradiated in a microwave reactor at 160° C. for one hour. The resulting solution was filtered through Celite®, washed with DCM, and concentrated. Purification (FCC) (MeOH(NH3)/DCM) gave the title compound (35 mg, 64%). MS (ESI): mass calculated for C22H23N7O, 401.20; m/z found 402.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.85 (s, 3H), 7.70 (d, J=6.7, 1H), 7.48-7.42 (m, 1H), 7.21 (d, J=4.4, 1H), 6.32-6.24 (m, 1H), 3.93-3.79 (m, 2H), 3.75-3.61 (m, 3H), 3.52 (s, 1H), 3.52-3.42 (m, 1H), 3.17 (dd, J=10.8, 5.0, 1H), 3.09-2.88 (m, 2H), 2.37-2.22 (m, 6H).

Workup

  1. customThe reaction was irradiated in a microwave reactor at 160° C. for one hour
  2. filtrationThe resulting solution was filtered through Celite®
  3. washwashed with DCM
  4. concentrationconcentrated
  5. customPurification (FCC) (MeOH(NH3)/DCM)

Sources & evidence

ORD record
ord-960cfe0fb97b4150a247be93c06bf644
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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