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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 624577
Notes
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Reaction equation

HRID 624577 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86722883(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

Product 1

HCID 86722903((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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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

  1. customquenched with water (20 mL)
  2. customThe phases were separated
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes