Hydrochloric Acid → 2-Amino-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 445047Notes

Reaction equation

HRID 445047 reaction equation
CN(C)CCCN(C)C.[NH2:10][C:11]1[N:16]=[C:15]([OH:17])[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=2)=[C:13]([CH3:28])[N:12]=1.[CH3:29][C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:31]=1[S:38](Cl)(=[O:40])=[O:39].Cl>C1COCC1.O.C(#N)C>[NH2:10][C:11]1[N:16]=[C:15]([O:17][S:38]([C:31]2[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=2[CH3:29])(=[O:40])=[O:39])[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=2)=[C:13]([CH3:28])[N:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8084N,N,N',N'-Tetramethyl-1,3-diaminopropaneHCID 130462-Mesitylenesulfonyl chlorideHCID 178433372HCID 178433372, compound

Product 1

HCID 866334092-Amino-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

N,N,N′,N′-Tetramethyl-1,3-propanediamine (56.7 g) was added dropwise to a suspension of the product from step (ii) (85.0 g) and 2,4,6-trimethylbenzenesulfonyl chloride (87.8 g) in THF (452.9 g), and the mixture was heated at 45° C. for 7 hours. 2.5% HCl in water (1291 g) was added to the mixture, and the mixture was stirred at 5° C. for 30 minutes. The resulting precipitate was collected by filtration, washed with acetonitrile (2×68.0 g), and dried to give the crude subtitle compound as a solid. A stirred suspension of the solid in acetonitrile (654.5 g) was heated at 70° C. for 30 minutes, cooled to 5° C. and stirred at 5° C. for 30 minutes. The resulting precipitate was collected by filtration, washed with acetonitrile (2×68.0 g) and dried to give the subtitle compound as a solid, 113.1 g; 1H NMR CDCl3: δ 7.24 (d, 2H), 7.11 (d, 2H), 6.96 (s, 2H), 4.71 (s, 2H), 3.90 (s, 2H), 3.71 (s, 2H), 2.59 (s, 6H), 2.32 (s, 3H), 2.27 (s, 3H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with acetonitrile (2×68.0 g)
  3. customdried
  4. customto give the crude subtitle compound as a solid
  5. temperaturewas heated at 70° C. for 30 minutes
  6. temperaturecooled to 5° C.
  7. stirringstirred at 5° C. for 30 minutes
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with acetonitrile (2×68.0 g)
  10. customdried

Sources & evidence

ORD record
ord-129e27ffe2ca4522a469fa4b806b43f9
Source dataset
uspto-grants-2013_07
Patent number
US08476288B2

Reaction notes

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