Diethylamine → HCID 10460190, compound

HRID 750814Notes

Reaction equation

HRID 750814 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)(=O)=O.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>C1COCC1>[CH2:36]([N:38]([C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)[CH2:39][CH3:40])[CH3:37]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 59753934HCID 59753934, compound

Product 1

HCID 10460190HCID 10460190, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Methylsulfonyl)-4-(3,4-difluorobenzyloxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 6, 55 mg, 0.10 mmol) was treated with excess diethylamine in THF according to the same general procedure described in Example 31, Step A. Workup (solvent removal under reduced pressure) and flash column chromatography on silica gel (eluted with 87/13 hexanes/ethyl acetate) afforded the title compound. HPLC/MS: m/e=550 (M++1); Rt=4.48 min. 1H-NMR 500 MHz (CDCl3): δ 1.23 (t, J=7 Hz, 3H), 3.65 (q, J=7 Hz, 2H), 5.39 (s, 2H), 7.04 (d, J=8 Hz, 2H), 7.08 (d, J=8 Hz, 2H), 7.13-7.22 (m, 5H), 7.34 (d, J=2 Hz, 1H).

Workup

  1. customWorkup (solvent removal under reduced pressure) and flash column chromatography on silica gel (eluted with 87/13 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9e2635a8ea5f473eb1a0c6f4a42a07e8
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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