Triethylamine → HCID 25095902, compound

HRID 2189114Notes

Reaction equation

HRID 2189114 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][NH:21]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:38][O:39][C:40](=[O:44])[CH2:41][CH2:42]Br>C1COCC1.ClCCl>[CH3:38][O:39][C:40](=[O:44])[CH2:41][CH2:42][N:21]1[CH2:22][CH2:23][CH2:24][CH:20]1[CH2:19][O:18][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76934Methyl 3-bromopropanoateHCID 58280184HCID 58280184, compound

Product 1

HCID 25095902HCID 25095902, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Dissolve 160 mg (0.4 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-4-(pyrrolidin-2-ylmethoxy)-furo[2,3-d]pyrimidine (Example 38A) in 0.8 ml of THF and add 110 μl (0.8 mmol) of triethylamine and 87 μl (0.8 mmol) of 3-bromopropionic acid methyl ester. Stir the mixture at 20-40° C. overnight, then dilute with dichloromethane and wash with saturated sodium hydrogencarbonate solution. Concentrate the solution under reduced pressure and purify the resulting oil by preparative RP-HPLC (eluent: acetonitrile/water gradient). 90 mg (44% of theory) of the target product are obtained.

Workup

  1. washwash with saturated sodium hydrogencarbonate solution
  2. concentrationConcentrate the solution under reduced pressure
  3. custompurify the resulting oil by preparative RP-HPLC (eluent: acetonitrile/water gradient)
  4. custom90 mg (44% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-b5da697559924f2c9cea1a1eb2b70e10
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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