1,4-Dioxane → HCID 59239310, compound

HRID 1697975Notes

Reaction equation

HRID 1697975 reaction equation
C(N1CC[C:15]2[C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:13][C:12]([C:24]3[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=3)=[N:11][C:10]=2C1)C1C=CC=CC=1.Cl[C:32]1[NH:37][C:36](=[O:38])[N:35]([CH3:39])[C:34](=[O:40])[CH:33]=1.O1[CH2:46][CH2:45]OCC1>>[CH2:12]([N:11]1[CH2:46][CH2:45][C:10]2[N:11]=[C:12]([C:24]3[CH:30]=[CH:29][C:27]([NH:28][C:32]4[NH:37][C:36](=[O:38])[N:35]([CH3:39])[C:34](=[O:40])[CH:33]=4)=[CH:26][CH:25]=3)[N:13]=[C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:15]=2[CH2:10]1)[C:24]1[CH:30]=[CH:29][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dioneHCID 67177362HCID 67177362, compound

Product 1

HCID 59239310HCID 59239310, compound

Procedure

4-(7-Benzyl-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline (0.0500 g, 0.000124 mol) Palladium(II) acetate (0.0043 g, 0.000019 mol) Cesium Carbonate (0.0921 g, 0.000283 mol) 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.0255 g, 0.0000441 mol) and 6-chloro-3-methylpyrimidine-2,4(1H,3H)-dione (0.0321 g, 0.000200 mol) were combined, nitrogen purged three times, added dry 1,4-Dioxane (0.88 mL, 0.011 mol) The reaction was microwaved on 300 watts, 120° C. for 160 minutes on a CEM microwave. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 10.36 (s, 1H), 8.53 (s, 1H), 8.27 (d, J=8.7, 2H), 7.42-7.34 (m, 4H), 7.28 (dd, J=15.1, 7.8, 3H), 5.01 (s, 1H), 3.72 (dd, J=9.7, 5.0, 6H), 3.55 (s, 2H), 3.50 (d, J=4.4, 4H), 3.08 (s, 3H), 2.68 (dd, J=18.0, 4.8, 4H). LC/MS-m/z+528.3 (M+H)+

Workup

  1. customnitrogen purged three times
  2. customwas microwaved on 300 watts, 120° C. for 160 minutes on a CEM microwave
  3. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-6b25c8d475134a15893ce714a539d621
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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