Water → HCID 86596303, compound

HRID 2117643Notes

Reaction equation

HRID 2117643 reaction equation
CC1C=CC=C(C)C=1C(C1C=C(OC)C=CC=1OC)N(C1C=CN=C([NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])=[CH:23][CH:22]=2)N=1)C(=O)[O-].[CH3:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[C:45]=1[O:51][C:52](=[O:72])[N:53]([C:65]1[CH:70]=[CH:69][N:68]=[C:67](Cl)[N:66]=1)[CH2:54][C:55]1[CH:60]=[C:59]([O:61][CH3:62])[CH:58]=[CH:57][C:56]=1[O:63][CH3:64].CN(C)CCOC1C=CC(N)=CC=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O>>[CH3:64][O:63][C:56]1[CH:57]=[CH:58][C:59]([O:61][CH3:62])=[CH:60][C:55]=1[CH2:54][N:53]([C:65]1[CH:70]=[CH:69][N:68]=[C:67]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])=[CH:25][CH:26]=2)[N:66]=1)[C:52](=[O:72])[O:51][C:45]1[C:46]([CH3:50])=[CH:47][CH:48]=[CH:49][C:44]=1[CH3:43]

Participants

7

Reactant 6

HCID 962WaterHCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 64846554-[2-(Dimethylamino)ethoxy]anilineHCID 11844763HCID 11844763, compoundHCID 86760734HCID 86760734, compound

Product 1

HCID 86596303HCID 86596303, compound

Conditions

Temperature
100 °C

Procedure

2,6-dimethylphenyl(2,5-bis(methyloxy)phenyl)methyl(2-((4-((2-(dimethylamino)ethyl)oxy)phenyl)amino)-4-pyrimidinyl)carbamate A resealable tube was charged with the (2-chloropyrimidin-4-yl)-(2,5-dimethoxy-benzyl)carbamic acid 2,6-dimethylphenyl ester (0.200 g, 0.467 mmol), 4-(2-dimethylaminoethoxy)phenylamine (0.088 g, 0.490 mmol), tris(dibenzylidene-acetone)-di-palladium (0.017 g, 0.019 mmol), 4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene (0.032 g, 0.056 mmol), and sodium carbonate (0.069 g, 0.653 mmol). The system was flushed with argon and toluene (3 mL) was added followed by the addition of water (0.010 mL, 0.467 mmol) (with stirring). The tube was flushed with argon and sealed. The mixture was heated at 100° C. for 16 h and then cooled to room temperature. The reaction mixture was filtered, and the filtrate was concentrated to afford a brown oil. The oil was purified via column chromatography (gradient elution with 0-100% dichloromethane-(90:10:1, dichloromethane/methanol/ammonium hydroxide)) to afford 2,6-dimethylphenyl (2,5-bis(methyloxy)phenyl)methyl(2-((4-((2-(dimethylamino)ethyl)oxy)-phenyl)amino)-4-pyrimidinyl)carbamate as a yellow solid. MS (MH+) 572.3; Calculated 571.67 for C32H37N5O5.

Workup

  1. customThe system was flushed with argon and toluene (3 mL)
  2. additionwas added
  3. customThe tube was flushed with argon
  4. customsealed
  5. temperaturecooled to room temperature
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated
  8. customto afford a brown oil
  9. customThe oil was purified via column chromatography (gradient elution with 0-100% dichloromethane-(90:10:1, dichloromethane/methanol/ammonium hydroxide))

Sources & evidence

ORD record
ord-0ab9cbbf6909488f9ed5c525d7a57102
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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