Tert-Butylamine → HCID 69284083, compound

HRID 1766102Notes

Reaction equation

HRID 1766102 reaction equation
CCN(C(C)C)C(C)C.[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:37][C:38]1[C:46]2[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([NH2:53])[CH:48]=3)=[N:44][C:43]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[N:42][C:41]=2[S:40][C:39]=1[C:60](O)=[O:61]>C(Cl)Cl.CN(C=O)C>[C:10]([NH:14][C:60]([C:39]1[S:40][C:41]2[N:42]=[C:43]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[N:44]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([NH2:53])[CH:48]=3)[C:46]=2[C:38]=1[NH2:37])=[O:61])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21109082HCID 21109082, compound

Product 1

HCID 69284083HCID 69284083, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (15.3 ml), tert-butylamine (9.3 ml) and TBTU (14.1 g) were added to a mixture of 5-amino-4-(3-aminophenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (example 31(f), 13.3 g) in a mixture of DCM (250 ml) and DMF (50 ml) under a nitrogen atmosphere. After 3 h at room temperature, the mixture was diluted with DCM and washed with sat. aq. NaHCO3, 0.1N aq. HCl and sat. aq. NaCl. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, using heptane/EtOAc=3/7 to 1/1 (v/v) as eluent.

Workup

  1. washwashed with sat. aq. NaHCO3, 0.1N aq. HCl and sat. aq. NaCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bb4b51eb0b2e4d37baabc2252ae25be5
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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