Triethylamine → 2-Bromo-6-methanesulfonyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

HRID 2066877Notes

Reaction equation

HRID 2066877 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][NH:10][CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([S:20]([CH3:19])(=[O:22])=[O:21])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 574611492-Bromo-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

Product 1

HCID 866550182-Bromo-6-methanesulfonyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-bromo-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (0.1 g, 0.47 mmol) and triethylamine (0.2 mL) in 2 mL of DCM, at 0° C., was added MsCl (0.1 mL). The mixture was stirred at room temperature for 1 h then diluted with 20 mL of DCM and washed with a mixture of saturated NaHCO3 (15 mL) and water (15 mL). The DCM was evaporated to afford the crude 59a.

Workup

  1. washwashed with a mixture of saturated NaHCO3 (15 mL) and water (15 mL)
  2. customThe DCM was evaporated

Sources & evidence

ORD record
ord-388d62471e3b4655ad46bc60b00eafa0
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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