Ammonium Chloride → HCID 21955963, compound

HRID 2212878Notes

Reaction equation

HRID 2212878 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26](OC)=[O:27])[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21955967HCID 21955967, compound

Product 1

HCID 21955963HCID 21955963, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxycarbonyl-phenyl)-amine (800 mg, 2.0 mmol) in tetrahydrofuran (25 ml) is added a solution of sodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (3 ml of a 3.5M solution) without cooling. The temperature of the reaction mixture rises to about +40° C. and the starting material dissolves immediately yielding a yellow clear solution. After an additional hour the solution is poured onto crushed ice and ammonium chloride. The colorless precipitate is filtered and washed with ethyl acetate and tetrahydrofuran. The organic phases are pooled, dried and concentrated under reduced pressure. Chromatography of the resulting solid gives the N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-hydroxymethyl-phenyl)-amine, m.p. 214–215° C.

Workup

  1. temperaturewithout cooling
  2. customrises to about +40° C.
  3. dissolutionthe starting material dissolves immediately
  4. customyielding a yellow clear solution
  5. additionAfter an additional hour the solution is poured
  6. filtrationThe colorless precipitate is filtered
  7. washwashed with ethyl acetate and tetrahydrofuran
  8. customdried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57f2b19d36c1476eb6283e8fe8c0da49
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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