Diisopropylethylamine → HCID 117678044, compound

HRID 1778179Notes

Reaction equation

HRID 1778179 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]=1.Cl.[C@H:14]12[CH2:20][C@H:17]([NH:18][CH2:19]1)[CH2:16][O:15]2.C(N(CC)C(C)C)(C)C>CN(C)C(=O)C>[Cl:8][C:6]1[N:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]=[C:2]([N:18]2[CH2:19][C@@H:14]3[CH2:20][C@H:17]2[CH2:16][O:15]3)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidineHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride

Product 1

HCID 117678044HCID 117678044, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4,6-dichloro-2-methylsulfonyl-pyrimidine (3.41 g, 15 mmol) and (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride (2.03 g, 15.0 mmol) in N,N-dimethylacetamide (40.5 mL), was added N,N-diisopropylethylamine (6.60 mL). The resulting mixture was stirred at room temperature. After 30 min, the reaction mixture was concentrated to a solid. The crude material was purified by column chromatography using an 80 g column, with a gradient of 0% to 100% ethyl acetate in heptane. The combined fractions containing product were concentrated under reduced pressure to provide (1S,4S)-5-(6-chloro-2-methylsulfonyl-pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (3.03 g). 1H NMR (400 MHz, Chloroform-d) δ 6.30 (s, 1H), 3.98-3.81 (m, 3H), 3.45-3.35 (m, 2H), 3.28 (s, 3H), 2.16-1.98 (m, 2H), 1.95-1.86 (m, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated to a solid
  2. customThe crude material was purified by column chromatography
  3. additionThe combined fractions containing product
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-012c456d8b2444e897d714b32017f11f
Source dataset
uspto-grants-2016_02
Patent number
US09266862B2

Reaction notes

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