Triethylamine → 6-chloro-5-fluoro-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

HRID 1366632Notes

Reaction equation

HRID 1366632 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.Cl.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:18][NH2:19].C(N(CC)CC)C>C1COCC1.O>[Cl:9][C:6]1[N:5]=[C:4]([S:10][CH3:11])[N:3]=[C:2]([NH:19][CH2:18][C:14]2[S:13][CH:17]=[CH:16][N:15]=2)[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 223782774,6-Dichloro-5-fluoro-2-(methylsulfanyl)pyrimidine2×HCID 42614216(1,3-Thiazol-2-yl)methanamine hydrochloride

Product 1

HCID 866370136-chloro-5-fluoro-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamineYield 117%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4,6-Dichloro-5-fluoro-2-(methylthio)pyrimidine (see Intermediate E) (0.422 g, 1.991 mmol), commercially available (1,3-thiazol-2-ylmethyl)amine hydrochloride (0.300 g, 1.992 mmol) and triethylamine (0.61 mL, 4.3765 mmol) were dissolved in THF (3 mL) and left to stir for 4 days. The reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated to produce 6-chloro-5-fluoro-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine as a yellow-orange solid (0.6773 g). LCMS: (M+H)+=291.0.

Workup

  1. waitleft
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee6c2258b3374310824c472e832215c2
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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