Triethylamine → HCID 25095901, compound

HRID 2189113Notes

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][CH:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]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:19]([O:18][C:16]2[C:17]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[C:10]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:11][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:20]1

Participants

Conditions

Temperature: 30 °C

Procedure

Dissolve 200 mg (0.5 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-4-(piperidin-3-yloxy)furo-[2,3-d]pyrimidine (Example 37A) in 1 ml of THF and add 69 μl (0.5 mmol) of triethylamine. After adding 54 μl (0.5 mmol) of 3-bromopropionic acid methyl ester, stir the mixture at 20-40° C. for approx. 8 h. In the meantime, add triethylamine (total of approx. 1.2 mmol) and 3-bromopropionic acid methyl ester (total of approx. 1.2 mmol) twice more. After diluting with dichloromethane, wash the mixture with saturated sodium hydrogencarbonate solution and concentrate under reduced pressure. Purify the crude product by means of preparative RP-HPLC (eluent: acetonitrile/water gradient). 118 mg (45.7% of theory) of the target product are obtained.

Workup

washwash the mixture with saturated sodium hydrogencarbonate solution
concentrationconcentrate under reduced pressure
customPurify the crude product by means of preparative RP-HPLC (eluent: acetonitrile/water gradient)
custom118 mg (45.7% of theory) of the target product are obtained

Sources & evidence

ORD record: ord-e9b760caf4604f06846af3e9f4191e63
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

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