Sodium Hydroxide → HCID 58233702, compound

HRID 1942116Notes

Reaction equation

HRID 1942116 reaction equation
Br[C:2]1[C:7]2[O:8][C:9]3([C:15]4[C:20]([C:6]=2[CH:5]=[CH:4][CH:3]=1)=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=4)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3.N1CCC[C@H]1C(O)=O.[CH3:30][S:31]([O-:33])=[O:32].[Na+].[OH-].[Na+]>CS(C)=O.[Cu]I>[CH3:30][S:31]([C:2]1[C:7]2[O:8][C:9]3([C:15]4[C:20]([C:6]=2[CH:5]=[CH:4][CH:3]=1)=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=4)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 58233690HCID 58233690, compound

Product 1

HCID 58233702HCID 58233702, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Copper (I) iodide (28 mg, 0.15 mmol, 0.4 eq) was added to a degassed solution of 7-bromospiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexan]-3-amine (44) (0.126 g, 0.36 mmol), (S)-pyrrolidine-2-carboxylic acid (0.034 g, 0.29 mmol), sodium methanesulfinate (0.074 g, 0.73 mmol) and sodium hydroxide (0.015 g, 0.36 mmol) in DMSO (1 mL) under Argon. The mixture was heated at 100° C., for 4 days. After workup, chromatography on silica gel afforded 15 mg of 7-(methylsulfonyl)spiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexan]-3-amine (45) as a brown solid. LCMS-ESI (POS), M/Z, M+1: Found 345.9.

Sources & evidence

ORD record
ord-614226dfee88497295acece3c37bf77a
Source dataset
uspto-grants-2013_03
Patent number
US08389533B2

Reaction notes

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