Sodium Carbonate → HCID 58878056, compound

HRID 2053080Notes

Reaction equation

HRID 2053080 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][OH:13])[CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].NCC(O)CO>C1(C)C=CC=CC=1.COCCOC.O1CCCC1.C(OCC)(=O)C.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.C(O)C>[CH3:9][S:8][C:6]1[N:5]=[C:4]([NH:10][CH2:11][CH2:12][OH:13])[CH:3]=[C:2]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:15]([F:26])([F:25])[F:14])[CH:21]=2)[N:7]=1

Participants

11

Reactant 4

HCID 10340Sodium CarbonateHCID 735613-Amino-1,2-propanediolHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 588780512-[[6-Chloro-2-(methylthio)-4-pyrimidinyl]amino]ethanol

Product 1

HCID 58878056HCID 58878056, compoundYield 33%

Reagents, catalysts & solvents 6

HCID 80711,2-DimethoxyethaneCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-(6-chloro-2-methylsulfanyl-pyrimidin-4-yl-amino)-ethanol (404 mg), 3-(trifluoromethyl)phenyl boronic acid (384 mg) and sodium carbonate (585 mg) in toluene (12 ml) with a few drops of DME and ethanol, was added Pd(PPh3)4 (106 mg). The resulting suspension was subjected to microwave heating at 150° C. for 20 mins. Reaction mixture was filtered through a celite pad, washed with ethyl acetate and concentrated in vacuo. The residual brown gum was columned on silica gel using heptane and ethyl acetate (1:1) as eluant. Product obtained was dissolved in tetrahydrofuran and stirred with 3-amino-1,2-propanediol at room temperature for 30 mins then diluted with ethyl acetate (40 ml) and washed with 1M hydrochloric acid (2×100 ml), brine (40 ml), dried over MgSO4 and concentrated in vacuo to give 200 mg of 2-[2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl-amino]-ethanol as a brown gum. Remaining acidic aqueous layer was slowly neutralised and the resulting white precipitate was filtered and dried. This generated 2-[2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl-amino]-ethanol as a white solid (450 mg).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through a celite pad
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customProduct obtained
  6. washwashed with 1M hydrochloric acid (2×100 ml), brine (40 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e42535312674120a707f033ce4a7997
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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