Triethylamine → HCID 117739183, compound

HRID 928557Notes

Reaction equation

HRID 928557 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[NH:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1>C(O)C>[C:11]1([C:10]2[C:3]3[C:2]([C:27]4([CH2:30][OH:31])[CH2:28][CH2:29][NH:24][CH2:25][CH2:26]4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 7087304-Chloro-5-phenylthieno[2,3-d]pyrimidine2×

Product 1

HCID 117739183HCID 117739183, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Chloro-5-phenyl-thieno[2,3-d]pyrimidine (1 g, 4.05 mmol) was dissolved in ethanol (15 ml) to give a yellow solution. To this was added triethylamine (1.7 ml, 12.2 mmol) and 4-piperidinemethanol (0.58 g, 5 mmol). The reaction mixture was heated to 50° C. and stirred for 1.5 hours until no 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine was present by TLC. The reaction mixture was allowed to cool to room temperature before being poured over ice water (50:50 mix). The resultant precipitate was collected by filtration to give the product as a pale yellow solid (1.23 g, yield 90%). LCMS: RT=4.05 min, M+1=326.

Workup

  1. customto give a yellow solution
  2. temperatureto cool to room temperature
  3. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-450f448838a04ee492bf6f4b3e514baf
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

Loading…