Tetrahydrofuran → HCID 21955962, compound

HRID 2212877Notes

Reaction equation

HRID 2212877 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)[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.C[Mg]Cl.[Cl-].[NH4+].[O:35]1CC[CH2:37][CH2:36]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][CH:36]([OH:35])[CH3:37])[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 21955967HCID 21955967, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 21955962HCID 21955962, compound

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 (30 ml) is added a solution of methyl magnesium chloride (6 ml of a 20% THF solution) without cooling. The temperature of the reaction mixture rises to about +45° 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-(2-hydroxy-2-methyl-ethyl)-phenyl]-amine, m.p. 219–220° C.

Workup

  1. temperaturewithout cooling
  2. customrises to about +45° 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-5d7e34af201e46a69f09c1d45516fbab
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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