Triethylamine → tert-Butyl 4-chloro-5,6-dihydropyrido(4',3':4,5)thieno(2,3-d)pyrimidine-7(8H)-carboxylate

HRID 38513Notes

Reaction equation

S1(CCCC1)(=O)=O.P(Cl)(Cl)([Cl:10])=O.C(N(CC)CC)C.O=[C:21]1[NH:26][CH:25]=[N:24][C:23]2[S:27][C:28]3[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:30][C:29]=3[C:22]1=2>[Cl-].[Na+]>[Cl:10][C:21]1[C:22]2[C:29]3[CH2:30][CH2:31][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][C:28]=3[S:27][C:23]=2[N:24]=[CH:25][N:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To sulfolane (3.19 L) was added phosphoryl chloride (785 g, 5.12 mol) at rt. Triethylamine (518 g, 5.12 mol) was added dropwise with water-bath cooling. tert-Butyl 4-oxo-3,5,6,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate from Example 10A (525.5 g, 1.706 mol) and additional sulfolane (1.34 L) were added, and the mixture was heated to 70° C. for 2.5 h. The mixture was cooled to it, and triethylamine (967 g, 9.56 mol) was added. A semi-saturated aqueous sodium chloride solution (10 L) was added during which the mixture was cooled with an ice-bath. After stirring at rt for 2 h, the precipitate was collected by suction filtration and washed three times with water (1.5 L). The residue was dried to yield 517 g (93%) of the title compound.

Workup

temperaturecooling
additionwas added
temperaturewas cooled with an ice-bath
filtrationthe precipitate was collected by suction filtration
washwashed three times with water (1.5 L)
customThe residue was dried

Sources & evidence

ORD record: ord-ff20f9553c854ecfb82a0143b2738d78
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

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