Dimethyl Sulfate → N-(Tetrahydro-2H-pyran-2-yloxy) 2-{6-[Methyl(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

HRID 2079784Notes

Reaction equation

HRID 2079784 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][NH:10][C:11]([C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:24][CH:23]3[CH:21]([CH:22]3[NH:25][S:26]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)(=[O:28])=[O:27])[CH2:20]2)=[N:17][CH:18]=1)=[O:12].S(OC)(O[CH3:43])(=O)=O.[Cl-].[NH4+]>CCCCCCC.C1COCC1.C(Cl)Cl>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][NH:10][C:11]([C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:20][CH:21]3[CH:23]([CH:22]3[N:25]([CH3:43])[S:26]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)(=[O:27])=[O:28])[CH2:24]2)=[N:17][CH:18]=1)=[O:12]

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59367684N-(Tetrahydro-2H-pyran-2-yloxy) 2-[6-(naphthalene-2-sulfonylamino)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxamide

Product 1

HCID 59367637N-(Tetrahydro-2H-pyran-2-yloxy) 2-{6-[Methyl(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

NaH (147 mg, 3.75 mmol) was washed with heptane, and suspended in THF (10 ml). N-(Tetrahydro-2H-pyran-2-yloxy) 2-[6-(naphthalene-2-sulfonylamino)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxamide (1.113 g, 2.2 mmol) was then added, followed by addition of dimethyl sulfate (0.22 ml, 2.3 mmol). The mixture was stirred for 48 h, then poured into DCM (150 ml). 2.4M ammonium chloride (50 ml) was added. The aqueous layer was further extracted with DCM (150 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give an orange oil. This was carried forward without any further purification.

Workup

  1. extractionThe aqueous layer was further extracted with DCM (150 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give an orange oil
  5. customThis was carried forward without any further purification

Sources & evidence

ORD record
ord-bbb881c216544d008d6435dd8a9e813f
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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