Triethylamine → HCID 86655315, compound

HRID 876962Notes

Reaction equation

HRID 876962 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=1.[O:13]1[CH2:17][CH2:16][C@H:15]([O:18][CH2:19][C:20]2[N:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[CH:22][CH:21]=2)[CH2:14]1.C(N(CC)CC)C>CC(O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]([NH:9][CH:10]=[O:11])=[C:6]([NH:27][CH2:26][C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:19][O:18][C@H:15]3[CH2:16][CH2:17][O:13][CH2:14]3)[N:25]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamideHCID 66718413HCID 66718413, compound

Product 1

HCID 86655315HCID 86655315, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (17.24 g, 82.46 mmol), 6-[(S)-(tetrahydrofuran-3-yl)oxymethyl]pyridin-2-ylmethylamine (18.89 g, 90.70 mmol) and triethylamine (12.64 mL, 90.70 mmol) in propan-2-ol (165 mL) was heated at reflux for 2 h, cooled and the resulting precipitate was filtered, washed with cold propan-2-ol and dried to give the title compound (22.66 g, 73%) as a pink solid; LC-MS retention time 1.46 min, (M+H)+ 379.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with cold propan-2-ol
  6. customdried

Sources & evidence

ORD record
ord-09f0bf71b2a04d4fae0aa2ecafac1b17
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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