Triethylamine → ((8R)-10-(5-Chlorofuran-2-yl)-5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazin-8-yl)methyl methanesulfonate

HRID 624577Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[O:11][C:10]([CH:12]2[C:17]3=[C:18]4[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:19]4=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)[N:16]3[CH2:15][C@H:14]([CH2:36][OH:37])[O:13]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][S:2]([O:37][CH2:36][C@@H:14]1[O:13][CH:12]([C:10]2[O:11][C:7]([Cl:6])=[CH:8][CH:9]=2)[C:17]2=[C:18]3[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:19]3=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[N:16]2[CH2:15]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (0.021 ml, 0.274 mmol) was added dropwise to a solution of (8R)-10-(5-chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione (Example 6, Step 3) (100 mg, 0.217 mmol), triethylamine (0.039 ml, 0.283 mmol) and DMAP (2.66 mg, 0.022 mmol) in DCM (2 mL). The mixture was stirred at 0° C. for 30 mins then diluted with DCM (20 ml) and quenched with water (20 mL). The phases were separated and the organic layer was dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Workup

customquenched with water (20 mL)
customThe phases were separated
dry with materialthe organic layer was dried over magnesium sulfate
customevaporated under vacuum

Sources & evidence

ORD record: ord-29821436ca3f405093b8c3ee804fd1d3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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