Diisopropylethylamine → (R)-1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluorophenyl)-2-methylpropan-2-ol

HRID 70089Notes

Reaction equation

HRID 70089 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[NH2:12][C@H:13]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:14]([CH3:17])([OH:16])[CH3:15].C(N(C(C)C)CC)(C)C>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C@H:13]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:14]([CH3:17])([OH:16])[CH3:15])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidineHCID 59708392(R)-1-amino-1-(4-fluorophenyl)-2-methylpropan-2-ol

Product 1

HCID 59708405(R)-1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluorophenyl)-2-methylpropan-2-olYield 28.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

533 mg 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine, 850 mg (R)-1-amino-1-(4-fluoro-phenyl)-2-methyl-propan-2-ol and 1.3 ml diisopropylethylamine are suspended in 9.8 ml dioxane. The reaction mixture is stirred for 2 hours in the microwave at 80° C. and then evaporated to dryness. The residue is mixed with water. The precipitate formed is suction filtered and purified by chromatography (silica gel, petroleum ether/ethyl acetate 100/0 to 60/40). 260 mg of the product are obtained as a solid.

Workup

  1. customevaporated to dryness
  2. additionThe residue is mixed with water
  3. customThe precipitate formed
  4. filtrationfiltered
  5. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate 100/0 to 60/40)

Sources & evidence

ORD record
ord-c65f4441ebe24b3aa40086ec83919b05
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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