Methylamine → HCID 86657452, compound

HRID 2096632Notes

Reaction equation

HRID 2096632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2([CH2:21][C:22]([O-:24])=O)[N:18]=[C:19]=[S:20].[CH3:25][NH2:26]>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3([CH2:21][C:22](=[O:24])[N:26]([CH3:25])[C:19](=[S:20])[NH:18]3)[CH2:6][CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:8][C:9]2=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86657453HCID 86657453, compound

Product 1

HCID 86657452HCID 86657452, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(6-bromo-4-isothiocyanato-2-phenylchroman-4-yl)acetate (192 mg, 0.46 mmol) in DCM (5 mL) is added a solution of 2 M MeNH2 in THF (1.3 mL), and stirred for 1 h. The solvent is removed under reduced pressure and the residue is dissolved in DCM (2 mL) and hexane (2 mL) and evaporated to afford 6-bromo-1′-methyl-2-phenyl-2′-thioxo-2′,3′-dihydro-1′H-spiro[chroman-4,4′-pyrimidin]-6′(5′H)-one as a white foam (209 mg), which is used for the next step without further purification. MS ESI +ve m/z 417 (M+H)+.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in DCM (2 mL)
  3. customhexane (2 mL) and evaporated

Sources & evidence

ORD record
ord-4427956d483c4f7a833ea7c15c223156
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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