Trifluoroacetic acid → 3,3,3-Trifluoro-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)propan-1-ol

HRID 2279559Notes

Reaction equation

HRID 2279559 reaction equation
[F:1][C:2]([F:25])([F:24])[CH:3]([NH:6][C:7]1[N:8]=[CH:9][C:10]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C:11]=2[N:12]=1)[CH2:4][OH:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:2]([F:1])([F:24])[CH:3]([NH:6][C:7]1[N:8]=[CH:9][C:10]2[CH2:16][CH2:15][NH:14][CH2:13][C:11]=2[N:12]=1)[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68294355tert-butyl 2-(1,1,1-trifluoro-3-hydroxypropan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Product 1

HCID 682952573,3,3-Trifluoro-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)propan-1-olYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 352 (53 mg, 0.15 mmol) in DCM (750 μL) at RT under nitrogen was added TFA (750 μL). The solution was stirred for 2 h and was then concentrated in a rotovap under high vacuum. The residue was redissolved in DCM (10 mL) and stirred rapidly with 1M Na2CO3 (10 mL) for 5 min. The layers were separated and the aqueous phase was extracted with DCM (2×10 mL). The combined extracts were dried (MgSO4), filtered and concentrated to afford 29 mg (76%) of 3,3,3-trifluoro-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)propan-1-ol (354) as a yellow foam.

Workup

  1. concentrationwas then concentrated in a rotovap under high vacuum
  2. dissolutionThe residue was redissolved in DCM (10 mL)
  3. stirringstirred rapidly with 1M Na2CO3 (10 mL) for 5 min
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with DCM (2×10 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-11429062f361428aab30bc64bcf89d8d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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