Cyanamide → (Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamide

HRID 2277747Notes

Reaction equation

HRID 2277747 reaction equation
BrN1C(=O)C2C(=CC=CC=2)C1=O.[CH2:13]([O:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28]1[C:33]([F:34])=[CH:32][N:31]=[C:30]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][S:43][CH3:44])[CH:37]=2)[N:29]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N:45]#[C:46][NH2:47].CC([O-])(C)C.[K+]>CO.C(Cl)Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH2:13]([O:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28]1[C:33]([F:34])=[CH:32][N:31]=[C:30]([NH:35][C:36]2[CH:37]=[C:38]([CH:39]=[CH:40][CH:41]=2)[CH2:42][S:43](=[N:47][C:46]#[N:45])[CH3:44])[N:29]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 9864CyanamideHCID 75542N-BromophthalimideHCID 23665647Potassium tert-butoxideHCID 894446014-[2-(Benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine

Product 1

HCID 89444507(Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

2-Bromo-1H-isoindole-1,3(2H)-dione (22.0 mg; 0.12 mmol) was added to a solution of 4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine (37.0 mg; 0.08 mmol), cyanamide (4.5 mg; 0.11 mmol) and potassium 2-methylpropan-2-olate (11.1 mg; 0.10 mmol) in MeOH (0.44 mL) at RT. The batch was stirred for 4 hours before it was diluted with DCM and aqueous sodium thiosulfate solution. The batch was extracted with DCM (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude (rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-λ4-sulfanylidene]-cyanamide that was used without further purification.

Workup

  1. extractionThe batch was extracted with DCM (2×)
  2. filtrationThe combined organic phases were filtered
  3. filtrationfilter
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e9f6b7f2e684585bd52bdc6bb16603e
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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