4-[2-(2-Amino-4-trifluoromethyl-pyrimidin-5-yl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester → 5-(7-Methyl-4-morpholino-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 391037Notes

Reaction equation

HRID 391037 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:20][C:19]([C:30]4[C:31]([C:37]([F:40])([F:39])[F:38])=[N:32][C:33]([NH2:36])=[N:34][CH:35]=4)=[N:18][C:17]=3[C:16]=2[CH3:41])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:41][C:16]1[C:17]2[N:18]=[C:19]([C:30]3[C:31]([C:37]([F:40])([F:39])[F:38])=[N:32][C:33]([NH2:36])=[N:34][CH:35]=3)[N:20]=[C:21]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:22]=2[S:23][C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 669342684-[2-(2-Amino-4-trifluoromethyl-pyrimidin-5-yl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582339795-(7-Methyl-4-morpholino-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl)-4-(trifluoromethyl)pyrimidin-2-amineYield 24%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 30 mg of 4-[2-(2-Amino-4-trifluoromethyl-pyrimidin-5-yl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester in 4.0 M of hydrogen chloride in 1,4-dioxane was stirred for 1 h. The mixture was evaporated. The product was purified by reverse phase HPLC to yield 6 mg of 323. MS (Q1) 495.2 (M)+.

Workup

  1. customThe mixture was evaporated
  2. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-acb3b1f9b56d4c89be89ea2c060261bb
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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