Water → HCID 59244954, compound

HRID 912109Notes

Reaction equation

HRID 912109 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27]N=4)[C:11]=3[N:12]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:14]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:31]([S-])C.[Na+].O.C(OCC)(=O)C>CN(C)C=O>[N:15]1([C:13]2[N:14]=[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)[C:10]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]4[CH:31]=[CH:27][N:28]=[CH:29][CH:30]=4)[C:11]=3[N:12]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4459711Sodium ethanethiolate2×HCID 67386328HCID 67386328, compound

Product 1

HCID 59244954HCID 59244954, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 4-(3-methoxyphenyl)-2-morpholin-4-yl-8-pyrimidin-4-yl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine (0.50 g, 1.24 mmol) in dimethylformamide (5 ml) was heated to 150° C., and sodium ethanethiolate (1.04 g, 12.4 mmol) was added for every 15 minutes in 3 portions. After heating at 150° C. for 2 hours, sodium ethanethiolate (1.04 g, 12.4 mmol) was added, followed by heating for further 15 minutes. After cooling the reaction mixture, water (5 ml) and ethyl acetate (20 ml) were added, to filter off the deposited precipitate. The crude product was purified by silica column chromatography (dichloromethane/methanol=95/5), to obtain the desired compound as a pale brown solid (0.21 g, 43% yield).

Workup

  1. temperatureby heating for further 15 minutes
  2. additionwere added
  3. filtrationto filter off the deposited precipitate
  4. customThe crude product was purified by silica column chromatography (dichloromethane/methanol=95/5)

Sources & evidence

ORD record
ord-668b0381dcaf4c2d8bef9d4d94bbe3a4
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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