Diisopropylamine → HCID 10099666, compound

HRID 750815Notes

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.[CH:36]([NH:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>>[CH:36]([N:39]([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:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]

Participants

Reactant 2

HCID 7912Diisopropylamine

HCID 59753934HCID 59753934, compound

Product 1

HCID 10099666HCID 10099666, compound

Procedure

2-(Methylsulfonyl)-4-(3,4-difluorobenzyloxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 6, 55 mg, 0.10 mmol) was reacted in neat diisopropyl amine heated at 150° C. overnight in a stainless steel pressure bottle by the general procedure described in Example 31, Step A. Workup (excess isopropyl amine removed under reduced pressure) and flash column chromatography on silica gel (eluted with 97/3 hexanes/ethyl acetate) afforded the title compound. HPLC: Rt=4.22 min. 1H-NMR 500 MHz (CDCl3): δ 1.28 (d, J=6 Hz, 6H), 4.217 (q, J=6 Hz, 1H), 5.39 (s, 2H), 7.04 (d, J=8 Hz, 2H), 7.08-7.14 (m, J=2H), 7.17 (m, 5H), 7.31 (d, J=2 Hz, 1H).

Workup

customWorkup (excess isopropyl amine removed under reduced pressure) and flash column chromatography on silica gel (eluted with 97/3 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-1cd6a64f0d0e4f0ba1d396d237f6c09b
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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