Triethylamine → HCID 12003973, compound

HRID 2219966Notes

Reaction equation

HRID 2219966 reaction equation
Cl.FC(F)(F)CC[N:6]1[CH2:15][CH2:14][C:13]2[C:12]([NH:16][C:17]3[CH:26]=[CH:25][C:20]4[O:21][CH2:22][CH2:23][O:24][C:19]=4[CH:18]=3)=[N:11][CH:10]=[N:9][C:8]=2[CH2:7]1.[C:29]1([CH3:38])[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1.C(N(CC)CC)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[O:21]1[CH2:22][CH2:23][O:24][C:19]2[CH:18]=[C:17]([NH:16][C:12]3[C:13]4[CH2:14][CH2:15][N:6]([C:31]5[CH:30]=[C:29]([CH3:38])[CH:34]=[CH:33][CH:32]=5)[CH2:7][C:8]=4[N:9]=[CH:10][N:11]=3)[CH:26]=[CH:25][C:20]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339503-Tolylboronic acidHCID 69222961HCID 69222961, compound

Product 1

HCID 12003973HCID 12003973, compoundYield 9.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[3,4-d]pyrimidin-4-amine from Example 7 (110 mg, 0.39 mmol) was dissolved in anhydrous THF (2 mL). To the mixture was added m-tolylboronic acid (105 mg, 0.78 mmol), Cu(OAc)2 (141 mg, 0.78 mmol) and triethylamine (0.68 g, 0.095 mL) and 390 mg of crushed, activated 4A moleculer seives. The mixture was agitated for 6 h and the solvent was removed under vacuum. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as reddish powder (14 mg, 9.6%).

Workup

  1. customof crushed
  2. customthe solvent was removed under vacuum
  3. customThe residue was purified

Sources & evidence

ORD record
ord-1ee9697ed658471eb337ffb912eac100
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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