Triethylamine → 2-[4-[4-(Methoxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]-1-pyrrolidin-1-yl-ethanone

HRID 928618Notes

Reaction equation

HRID 928618 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][S:20][C:12]=3[N:13]=[C:14]([CH2:16][C:17](O)=[O:18])[N:15]=2)[CH2:6][CH2:5]1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]3[C:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][S:20][C:12]=3[N:13]=[C:14]([CH2:16][C:17]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:18])[N:15]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 895793932-[4-[4-(Methoxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]acetic acid

Product 1

HCID 895793662-[4-[4-(Methoxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]-1-pyrrolidin-1-yl-ethanoneYield 11.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[4-[4-(Methoxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]acetic acid (24 mg, 0.06 mmol), pyrrolidine (5 mg, 0.067 mmol), HATU (26 mg) and triethylamine (0.025 mL) were stirred in acetonitrile (2 mL) at 50° C. for 20 hrs. The reaction was partitioned between water and DCM. The organics were separated and concentrated in vacuo. The residue was purified by preparative TLC, eluting 10% methanol in DCM. The isolated band was repurified by preparative TLC, eluting ethyl acetate to give 2-[4-[4-(methoxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]-1-pyrrolidin-1-yl-ethanone (3 mg). LCMS RT=4.61 min. M+1=451.

Workup

  1. customThe reaction was partitioned between water and DCM
  2. customThe organics were separated
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC
  5. washeluting 10% methanol in DCM
  6. customThe isolated band was repurified by preparative TLC
  7. washeluting ethyl acetate

Sources & evidence

ORD record
ord-4b66cc926c9d470ea23d89b3beec2a1f
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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