Triethylamine → HCID 42610049, compound

HRID 384624Notes

Reaction equation

HRID 384624 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[CH:3]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1.C(N(CC)CC)C>CN1CCCC1=O>[NH2:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[N:13][CH:12]=[CH:11][N:10]=3)[CH:3]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 59613383HCID 59613383, compound

Product 1

HCID 42610049HCID 42610049, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-chloro-N-(pyrazin-2-yl)pyrimidin-4-amine (20 mg, 0.096 mmol), tert-butyl N-(4-piperidinylmethyl)carbamate (41 mg, 0.193 mmol) and triethylamine (27 μL, 0.193 mmol) in 1-methyl-2-pyrrolidinone (1 mL) was heated at 140° C. for 10 minutes using microwave irradiation. The mixture was concentrated in vacuo and the residue purified using preparative HPLC. The purified solid was dissolved in dichloromethane (4 mL) and treated with trifluoroacetic acid (4 mL) for 1 hour at room temperature. The solution was applied to a MP-TsOH SPE cartridge, washed, then eluted with 2N ammonia and concentrated to give N-(6-(4-(aminomethyl)piperidin-1-yl)pyrimidin-4-yl)pyrazin-2-amine (4.4 mg, 16%).

Workup

  1. custommicrowave irradiation
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified
  4. dissolutionThe purified solid was dissolved in dichloromethane (4 mL)
  5. additiontreated with trifluoroacetic acid (4 mL) for 1 hour at room temperature
  6. washwashed
  7. washeluted with 2N ammonia
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0cdf7c1d405b4f9bb597e76049e6e077
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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